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A composite film of Ni(II) phthalocyanine bearing four benzothiazole (bs) substituents (2) and carboxylic-functionalised multi-walled carbon nanotubes (2-f-MWCNTs) was drop cast on an Au electrode and heated at 50 °C to form a new Au|2-f-MWCNTs sensor for detection of Hg(II) ions. The redox potentials of 2 were measured by cyclic voltammetry, and the processes were affirmed spectroelectrochemically. The nanocomposite of the 2-f-MWCNTs was characterised by Fourier transform Infrared and Raman spectroscopies, and Scanning electron Microscopy. Its electrocatalysis towards Hg(II) was probed by various voltammetric techniques showing higher Faradaic currents in standard redox solutions than the bare or SAMs of 2. Anodic stripping voltammgrams of Hg2+ ions at the Au|2-f-MWCNTs showed good electrocatalytic activity with a linear range spanning 14.4 μM and 1000 μM, and a precision of ± 4.2%. Electrode selectively detected Hg2+ ions in the presence of Pb2+ and Zn2+ ions, while its SWV scan for a mixture of Hg2+ and Cd2+ showed high background noise. [ABSTRACT FROM AUTHOR]

Introduction: Benzotriazoles and benzothiazoles (BTs) are high-production volume chemicals as well as widely distributed emerging pollutants with potential health risk. However, information about human exposure to BTs and associated health outcomes is limited. Objective: We aimed to characterise exposure to BTs among Czech men, including possible occupational exposure among firefighters, its predictors, and its associations with liver function, serum lipids and oxidative stress. Methods: 165 participants (including 110 firefighters) provided urine and blood samples that were used to quantify the urinary levels of 8 BTs (high-performance liquid chromatography-tandem mass spectrometry), and 4 liver enzymes, cholesterol, low-density lipoprotein, and 8-hydroxy-2'-deoxyguanosine. Linear regression was used to assess associations with population characteristics and biomarkers of liver function, serum lipids and oxidative stress. Regression models were adjusted for potential confounding variables and false discovery rate procedure was applied to account for multiplicity. Results: The BTs ranged from undetected up to 46.8 ng/mL. 2-hydroxy-benzothiazole was the most predominant compound (detection frequency 83%; median 1.95 ng/mL). 1-methyl-benzotriazole (1M-BTR) was measured in human samples for the first time, with a detection frequency 77% and median 1.75 ng/mL. Professional firefighters had lower urinary 1M-BTR compared to non-firefighters. Urinary 1M-BTR was associated with levels of γ-glutamyl transferase (β = − 17.54%; 95% CI: − 26.127, − 7.962). Conclusion: This is the first study to investigate BT exposure in Central Europe, including potentially exposed firefighters. The findings showed a high prevalence of BTs in the study population, the relevance of 1M-BTR as a new biomarker of exposure, and an urgent need for further research into associated adverse health outcomes. [ABSTRACT FROM AUTHOR]

Herein, we report the synthesis and characterization of the novel 2‐aminoguanidine‐derived Schiff base rhenium(I) compounds: fac‐[Re(CO)3(Hguabs)Br]Br (1) (Hguabs ⋅ Cl=2‐((benzothiazole)methyleneamino)guanidine chloride) and fac‐[Re(CO)3(guaquin)Br] (2) (guaquin=2‐((quinolin‐2‐yl)methyleneamino)guanidine). [ABSTRACT FROM AUTHOR]

Diarrhea remains one of the leading causes of mortality worldwide, especially among children. Accumulated evidence has shown that Shigella species are the most prevalent bacteria responsible for diarrhea in developing countries. Antimicrobial therapy is necessary for Shigella infections; however, the development of resistance against current drugs justifies the pressing need to search for alternative medications. In this study, we have applied antibacterial phenotypic screening to identify potent anti-Shigella compounds across a broad chemical diversity, including selected acetaminophen derivatives containing a benzothiazole backbone, and their combination with certain antibiotics. As a result, two acetaminophen derivatives containing a benzothiazole backbone (4a and 4b) inhibited the growth of Shigella flexneri with a common MIC value of 12.5 µg/mL. These compounds were established through a time-kill kinetics study to be potentially bactericidal. Meanwhile, the 2-aminobenzothiazoles (1a and 1b) used for the synthesis of compounds 4 (a and b) were found to be poorly active (MIC: 100 µg/mL) against this pathogen. Combination studies of 4a and 4b with the least effective antibiotics (ceftriaxone and cotrimoxazole) demonstrated synergistic anti-Shigella activity with MIC values decreasing from 12.5 to 0.781 μg/ mL. The present study demonstrates that the azobenzothiazole dyes 4 (a and b) can be repurposed as potential anti-Shigella compounds, thus providing potential chemical pharmacophores for the discovery of drugs against infectious diarrhea caused by Shigella and other enteric pathogens, especially in developing countries. [ABSTRACT FROM AUTHOR]

In this study, Schiff bases (SCH-1 and SCH-2) were synthesized from the condensation reaction of 2-aminobenzothiazole with 3-hydroxy-4-methoxybenzaldehyde and 3-hydroxy-4-ethoxybenzaldehyde. Poly(phenoxy-imine)s were synthesized from Schiff bases via oxidative polycondensation by NaOCl (6–14% aqueous solution) as oxidant in alkaline medium and H2O2 (35% aqueous solution) as oxidant in THF medium. The structures characterizations of Schiff bases and poly(phenoxy-imine)s were confirmed by FT-IR, 1H and 13C NMR, CV, UV–Vis and TGA analyses. Limit oxygen index (LOI) and the heat resistance index (THRI) temperature were determined from thermogravimetric measurements of compounds. P-SCH-2-A showed the highest LOI as 45.50 with self-extinguishing according to other polymers (18–30). The optical band gap of P-SCH-2-A was determined to be 1.99 eV. Additionally, the optical band gap energy of compounds were calculated by using the Tauc method. According to the Tauc method, the optical band gap (Eg) value of P-SCH-2-A was calculated to be 2.20 eV. The glass transition temperatures (Tg) and surface properties of poly(phenoxy-imine)s were determined from DSC and SEM analyses, respectively. The weight average molecular weight (Mw) values of P-SCH-1-O, P-SCH-2-O, P-SCH-1-A and P-SCH-2-A were calculated to be 7400, 8400, 3100 and 19,100 g mol−1 from gel permeation chromatography (GPC) measurements. [ABSTRACT FROM AUTHOR]

In this study, the synthesis of N‐(5,6‐methylenedioxybenzothiazole‐2‐yl)‐2‐[(substituted)thio/piperazine]acetamide/propanamide derivatives (3a‐3k) and to investigate their acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and β‐secretase 1 (BACE‐1) inhibition activity were aimed. Mass, 1H NMR, and 13C NMR spectra were utilized to determine the structure of the synthesized compounds. Compounds 3b, 3c, 3f, and 3j showed AChE inhibitory activity which compound 3c (IC50 = 0.030 ± 0.001 µM) showed AChE inhibitory activity as high as the reference drug donepezil (IC50 = 0.0201 ± 0.0010 µM). Conversely, none of the compounds showed BChE activity. Compounds 3c and 3j showed the highest BACE‐1 inhibitory activity and IC50 value was found as 0.119 ± 0.004 µM for compound 3j whereas IC50 value was 0.110 ± 0.005 µM for donepezil, which is one of the reference substance. Molecular docking studies have been carried out using the data retrieved from the server of the Protein Data Bank (PDBID: 4EY7 and 2ZJM). Using in silico approach behavior active compounds (3c and 3j) and their binding modes clarified. [ABSTRACT FROM AUTHOR]

In this study, the residue of toxic 2-mercaptobenzothiazole, a semi-volatile heteroaromatic, was extracted from wastewater using a new spectrofluorometric method. The method is based on measuring 2-Mercaptobenzothiazole the quenching effect on the fluorescence intensity of ZnS quantum dot–gelatin nanocomposite in (pH 4, λex 310 and λem 345 nm, in time 60 s). Different factors affecting the reaction were studied and optimized. The calibration plot is linear in the concentration range of (0.05–10.0 µgL−1). The relative standard deviations and the detection limit of the method were ±1.0% and 0.05 μgL−1, respectively. Observed, outcomes confirmed the suitability recovery and a meager detection limit for analyzing toxic 2-Mercaptobenzothiazole in water samples. The preliminary results from this study demonstrate that this new method can be used to analyze 2-mercaptobenzothiazole in wastewater. [ABSTRACT FROM AUTHOR]

Background: Benzothiazole derivatives have been reported to possess a wide range of biological activities, including antimalarial activity. This systematic review aims to summarize and evaluate the antimalarial activities of benzothiazole analogs. Methods: We conducted an electronic search using nine databases in October 2017 and subsequently updated in September 2022. We included all original in vitro and in vivo studies that documented the antimalarial activities of compounds containing benzothiazole analogs with no restriction. The risk of bias of each included study was assessed by ToxRTool. Results: Twenty‐eight articles were included in our study, which are in vitro, in vivo, or both. Of these, 232 substances were identified to have potent antiplasmodial activity against various strains of the malaria parasite. Benzothiazole analogs show different antimalarial mechanisms, including inhibition of Plasmodium falciparum enzymes in in vitro studies and inhibition of blood parasites in in vivo studies. Conclusions: Benzothiazole derivatives are promising substances for treating malaria. The structure–activity relationship studies suggest that the substitution pattern of the benzothiazole scaffold plays a crucial role in determining the antimalarial activity of the analog. [ABSTRACT FROM AUTHOR]

The catalytic performance for electrocatalytic CO2 reduction reaction (CO2RR) depends on the binding strength of the reactants and intermediates. Covalent organic frameworks (COFs) have been adopted to catalyze CO2RR, and their binding abilities are tuned via constructing donor‐acceptor (DA) systems. However, most DA COFs have single donor and acceptor units, which caused wide‐range but lacking accuracy in modulating the binding strength of intermediates. More elaborate regulation of the interactions with intermediates are necessary and challenge to construct high‐efficiency catalysts. Herein, the three‐component COF with D‐A‐A units was first constructed by introducing electron‐rich diarylamine unit, electron‐deficient benzothiazole and Co‐porphyrin units. Compared with two‐component COFs, the designed COF exhibit elevated electronic conductivity, enhanced reducibility, high efficiency charge transfer, further improving the electrocatalytic CO2RR performance with the faradic efficiency of 97.2 % at −0.8 V and high activity with the partial current density of 27.85 mA cm−2 at −1.0 V which exceed other two‐component COFs. Theoretical calculations demonstrate that catalytic sites in three‐component COF have suitable binding ability of the intermediates, which are benefit for formation of *COOH and desorption of *CO. This work offers valuable insights for the advancement of multi‐component COFs, enabling modulated charge transfer to improve the CO2RR activity. [ABSTRACT FROM AUTHOR]

The catalytic performance for electrocatalytic CO2 reduction reaction (CO2RR) depends on the binding strength of the reactants and intermediates. Covalent organic frameworks (COFs) have been adopted to catalyze CO2RR, and their binding abilities are tuned via constructing donor‐acceptor (DA) systems. However, most DA COFs have single donor and acceptor units, which caused wide‐range but lacking accuracy in modulating the binding strength of intermediates. More elaborate regulation of the interactions with intermediates are necessary and challenge to construct high‐efficiency catalysts. Herein, the three‐component COF with D‐A‐A units was first constructed by introducing electron‐rich diarylamine unit, electron‐deficient benzothiazole and Co‐porphyrin units. Compared with two‐component COFs, the designed COF exhibit elevated electronic conductivity, enhanced reducibility, high efficiency charge transfer, further improving the electrocatalytic CO2RR performance with the faradic efficiency of 97.2 % at −0.8 V and high activity with the partial current density of 27.85 mA cm−2 at −1.0 V which exceed other two‐component COFs. Theoretical calculations demonstrate that catalytic sites in three‐component COF have suitable binding ability of the intermediates, which are benefit for formation of *COOH and desorption of *CO. This work offers valuable insights for the advancement of multi‐component COFs, enabling modulated charge transfer to improve the CO2RR activity. [ABSTRACT FROM AUTHOR]

Treatment of the Schiff base 2-N-(salicylidene) benzothiazole (SabtH) with palladium chloride afforded the neutral 2-N-(salicylidene) benzothiazole palladium(II) complex. This was then treated with one molar equivalent of either ethylenediamine or 1,10-phenanthroline, yielding the neutral mixed ligand complexes 1 and 2, respectively. The prepared organic ligand and its mixed ligand complexes were characterised via UV-Vis, FTIR, ¹H-NMR, and 13C-NMR spectroscopy. The antiproliferative activities of 1 and 2 were tested against MCF-7 (breast) and HT-29 (colon) cancer cells using an MTT assay. 1 showed strong antiproliferative activity against both MCF-7 and HT-29 cancer cells, with IC50 values of 74.6 ± 8.35 and 174 ± 20.28 µg/mL, respectively. In addition, 2 exhibited the maximum antioxidant activity, with an EC50 value of 1029 ± 196.76 µg/mL. [ABSTRACT FROM AUTHOR]

The chemical reaction of 4-bromo-benzoyl-chloride and 2-amino-thia-zole in the presence of potassium thio-cyanate yielded a white solid formulated as C15H10BrN3OS2, which consists of 4-bromo-benzamido and 2-benzo-thia-zolyl moieties connected by a thio-urea group. The 4-bromo-benzamido and 2-benzo-thia-zolyl moieties are in a trans conformtion (sometimes also called s-trans due to the single bond) with respect to the N-C bond. The dihedral angle between the mean planes of the 4-bromo-phenyl and the 2-benzo-thia-zolyl units is 10.45 (11)°. The thio-urea moiety, -C-NH-C(=S) -NH- fragment forms a dihedral angle of 8.64 (12)° with the 4-bromo-phenyl ring and is almost coplanar with the 2-benzo-thia-zolyl moiety, with a dihedral angle of 1.94 (11)°. The mol-ecular structure is stabilized by intra-molecular N-H⋯O hydrogen bonds, resulting in the formation of an S(6) ring. In the crystal, pairs of adjacent mol-ecules inter-act via inter-molecular hydrogen bonds of type C-H⋯N, C-H⋯S and N-H⋯S, resulting in mol-ecular layers parallel to the ac plane. [ABSTRACT FROM AUTHOR]

The article discusses the synthesis of thiazole-fused tricyclic quinazolinone alkaloids and their derivatives, focusing on compounds found in traditional Chinese and Indian herbal medicine. The authors describe their synthetic program and the successful synthesis of various thiazole-fused tricyclic quinazolinones. The article provides information on the physical and chemical properties of the synthesized compounds, including melting points, yields, and spectral analysis results. This information can be useful for researchers studying these compounds and their potential applications. [Extracted from the article]

The highly efficient synthesis of benzoxazole, benzothiazole and benzimidazole has attracted much attention due to their superior biological activities. However, developing environmentally friendly and poisoning-resistant catalysts in heterogeneous catalytic systems remains a critical challenge. Herein, an atomically dispersed Co1/NC catalyst was fabricated by facile pyrolysis of a zeolitic imidazolate framework (ZnCo-ZIF). The Co1/NC catalyst exhibited excellent oxidation catalysis, sulfur-resistance and reusability performance. The mass specific activity (MSA) of Co1/NC was up to 42.0 mol2-PBO molCo−1 h−1, much higher than that of the Co/NC nano-catalyst (15.6 mol2-PBO molCo−1 h−1). Mechanism studies showed that O2 was activated by atomically dispersed Co active species to form 1O2 and ˙O2−, which were responsible for the dehydrogenation of the key imine intermediates to produce 2-phenylbenzoxazole (2-PBO). The current work represents a novel feasible strategy for the synthesis of bioactive heterocyclic compounds using efficient, stable and green heterogeneous catalysts. [ABSTRACT FROM AUTHOR]

Inhibitors of Decaprenylphosphoryl‐β‐D‐ribose 2′‐epimerase (DprE1) are being thoroughly explored as potential pharmacological entities for the development of new anti‐tubercular therapeutics. In this context, benzothiazole‐bearing compounds have emerged as potential non‐covalent DprE1 inhibitors active against mycobacterium tuberculosis. In view of the promising anti‐tubercular activity of benzothiazole based non‐covalent DprE1 inhibitor TCA1; a series of thirty small peptide conjugates of benzothiazole‐2‐carboxylic acid has been synthesized and evaluated for their anti‐tubercular activity against the M.tb H37Ra strain by broth microdilution assay. Among the compounds tested, compounds methyl (6‐methoxybenzo[d]thiazole‐2 carbonyl)tryptophylalaninate and methyl (6‐methylbenzo[d]thiazole‐2‐carbonyl)tryptophylalaninate demonstrated potential anti‐tubercular activity with minimum inhibitory concentration (MIC) values of 4 and 8 μg/mL, respectively. These compounds were further identified to be mycobactericidal and are completely killing the microbes at 8‐16 μg/mL concentrations. Furthermore, the cytotoxicity study of most potent compound methyl (6‐methoxybenzo[d]thiazole‐2 carbonyl)tryptophylalaninate illustrated no significant toxicity to the human cell line HepG2. Moreover, synthesised compounds were subject to molecular docking, ADME studies and MM‐GBSA calculations. In silico studies suggest that these compounds show strong interactions with key amino acids in the binding pocket of DprE1 (PDBID: 4KW5) with the most active conjugates residing well (with docking scores of −08.49 and −7.902 kcal/mol). [ABSTRACT FROM AUTHOR]

The work presented in the manuscript describes a simple strategy for transforming thermally activated delayed fluorescent organic light‐emitting diodes (TADF OLEDs) compound 10‐(dibenzo[a,c]phenazin‐11‐yl)‐10H‐phenoxazine (DPZ‐PXZ) into type I photosensitizer 10‐(dibenzo[a,c]phenazin‐11‐yl)‐10H‐phenothiazine (DPZ‐PHZ) by strategically introducing sulfur atom in the photosensitizing core. The synthesized compound DPZ‐PHZ exhibits aggregation‐induced enhancement (AIE) and through‐space charge transfer (TSCT) characteristics and generates red emissive assemblies in mixed aqueous media. The original compound DPZ‐PXZ exhibits well‐separated HOMO and LUMO levels and is reported to have highly efficient reverse intersystem crossing (RISC). In comparison, the incorporation of sulfur atom in the phenothiazine donor regulates the electronic communication between donor and acceptor units and promotes the intersystem crossing (ISC) in DPZ‐PHZ molecules. Interestingly, compound DPZ‐PHZ exhibits rapid activation of aerial oxygen for instant generation of superoxide radical anion. Backed by excellent type I photosensitizing activity, DPZ‐PHZ assemblies have high catalytic potential for the synthesis of benzimidazoles, benzothiazoles and quinazolines derivatives under mild reaction conditions. The work presented in the manuscript provides an insight into the combination of heavy atom approach and TSCT for achieving adequate electronic communication between donor and acceptor units, balanced RISC/ISC, and stabilized‐charge separated state for the development of efficient type I photosensitizing assemblies. [ABSTRACT FROM AUTHOR]

AbstractThe adsorption performance of 2-mercaptobenzothiazole from an aqueous solution on activated carbon synthesized through grape marc was explored. In this research, the agricultural waste was chemically treated with phosphoric acid (40% H3PO4, 170 °C, 3 h), then pyrolyzed at 650 °C for 2 h, to obtain the GMAC-650 to be used as an adsorbent. The resulting material was characterized by Fourier-transform infrared spectroscopy, X-ray diffraction, and Brunauer–Emmett–Teller (BET). Maximum uptake (∼99%) is obtained under ideal conditions: an adsorbent dose of 0.8 g L−1 and pH = 8 for an initial concentration of 10 mg L−1 at 45 °C. The adsorption equilibrium data were fitted to the following isotherm models: Langmuir and Freundlich. For optimal equilibrium isotherm selection, a comparison of linear and non-linear methods for the adsorption of MBT. It was based on four error functions: the coefficient of determination R2, the sum of squared errors, the Chi-square (χ2), and the root mean square error. The current work has shown that the non-linear method is a more adequate method for estimating the parameters of the isotherm compared with the linear method. The comparative analysis of the models shows that the Freundlich model is more appropriate for describing equilibrium data. [ABSTRACT FROM AUTHOR]

ctive: Benzothiazole and imidazo[2,1-b][1,3,4]thiadiazole derivatives are the most important pharmacophores and intermediates for making drugs. This study focuses on the preparation and anti-cancer activity of novel benzothiazole-based imidazo[2,1-b][1,3,4]thiadiazole scaffolds. Methods: The synthesized benzothiazolebased imidazo[2,1-b][1,3,4]thiadiazole scaffolds (Va–Vi) were evaluated. The anticancer activity of (Va–Vi) against MCF-7 and A549 cell lines was determined using the MTT assay and screened with in silico molecular docking studies. Results and Discussion: Compounds 2-(6-(4-chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl)benzo[d]thiazole (Vb), 2-(6-(4-bromophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl)benzo[d]thiazole (Vd), and 2-(6-(4nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl)benzo[d]thiazole (Vh) exhibited the most potent anticancer activity against MCF-7 and A549 cancer cell lines. Molecular docking studies of all synthesized compounds and erlotinib were also carried out on the EGFR receptor, showing that compounds (Vb), (Vd), and (Vh) had significantly higher binding scores and inhibitory constants than the reference drug erlotinib. Conclusions: It has been observed that the substitution on the 4-chlorophenyl ring (Vb), 4-bromophenyl ring (Vd), and 4-nitrophenyl ring (Vh) is important for maintaining their anticancer activity. The outcomes of the kinase inhibitory assay of these significant (Vb), (Vd), and (Vh) hybrids against the tyrosine kinase EGFR strongly corroborated the in vitro anticancer findings and the in silico docking investigations. The investigation demonstrated that the newly synthesized compounds have the potential as anticancer agents and provided leads for further development. [ABSTRACT FROM AUTHOR]

Glucocorticoids (GCs) act through the glucocorticoid receptor (GR) and are commonly used as anti-inflammatory and immunosuppressant medications. Chronic GC use has been linked with unwanted complications such as steroid-induced diabetes mellitus (SIDM), although the mechanisms for these effects are not completely understood. Modification of six GC parent molecules with 2-mercaptobenzothiazole resulted in consistently less promoter activity in transcriptional activation assays using a 3xGRE reporter construct while constantly reducing inflammatory pathway activity. The most selective candidate, DX1, demonstrated a significant reduction (87%) in transactivation compared to commercially available dexamethasone. DX1 also maintained 90% of the anti-inflammatory potential of dexamethasone while simultaneously displaying a reduced toxicity profile. Additionally, two novel and highly potent compounds, DX4 and PN4, were developed and shown to elicit similar mRNA expression at attomolar concentrations that dexamethasone exhibits at nanomolar dosages. To further explain these results, Molecular Dynamic (MD) simulations were performed to examine structural changes in the ligand-binding domain of the glucocorticoid receptor in response to docking with the top ligands. Differing interactions with the transcriptional activation function 2 (AF-2) region of the GR may be responsible for lower transactivation capacity in DX1. DX4 and PN4 lose contact with Arg611 due to a key interaction changing from a stronger hydrophilic to a weaker hydrophobic one, which leads to the formation of an unoccupied channel at the location of the deacylcortivazol (DAC)-expanded binding pocket. These findings provide insights into the structure–function relationships important for regulating anti-inflammatory activity, which has implications for clinical utility. [ABSTRACT FROM AUTHOR]

We report an efficient and simple method for the synthesis of core–shell quantum dots CdSe/CdS in aqueous media under normal pressure. This QDs was successfully loaded on the surface of titanium dioxide nanotubes (TNTs) to get the QDs/TNTs composite photocatalysts. The QDs/TNTs composites were successfully applied to the cyclization reaction between arylamines and a series of aldehydes to give the corresponding N-heterocyclic compounds. The results show that the QDs/TNTs composite with the advantages of good catalytic activity, low cost, ease of recovering, and being able to be used for several times. [ABSTRACT FROM AUTHOR]

A new approach for synthesizing triazole rings through the application of laccases, copper containing oxidoreductase enzymes is outlined. A series of benzothiazoles and benzimidazoles-functionalized alkynes were initially synthesized utilizing a biocatalysis laccase-based approach. The resultant alkynes were further treated with aryl azides in a 1,3-dipolar cycloaddition reaction facilitated by laccase enzymes to obtain 1,2,3-triazole-fused benzothiazoles and benzimidazoles. [ABSTRACT FROM AUTHOR]

Eight QSAR models (M1–M8) were developed from a dataset of 118 benzo-fused heteronuclear derivatives targeting VEGFR-2 by Monte Carlo optimization method of CORALSEA 2023 software. Models were generated with hybrid optimal descriptors using both SMILES and Graphs with zero- and first-order Morgan extended connectivity index from a training set of 103 derivatives. All statistical parameters for model validation were within the prescribed limits, establishing the models to be robust and of excellent quality. Among all models, split-2 of M5 was the best-fit as reflected by ${\rm{ }}r_{{\rm{validation}}}^2$ r v a lidation 2 , ${\rm{ }}Q_{{\rm{validation}}}^2$ Q v a lidation 2 and ${\rm{MAE}}$ MAE . Mechanistic interpretation of this model assisted the identification of structural descriptors as promoters and hinderers for VEGFR-2 inhibition. These descriptors were utilized to design novel VEGFR-2 inhibitors (YS01-YS07) by bringing modifications in compound MS90 in the dataset. Docking of all designed compounds, MS90 and sorafenib with VEGFR-2 binding site revealed favourable binding interactions. Docking score of YS07 was higher than that of MS90 and sorafenib. Molecular dynamics simulation study revealed sustained interactions of YS07 with key amino acids of VEGFR-2 at a run time of 100 ns. This study concludes the development of a best fit QSAR model which can assist the design of new anticancer agents targeting VEGFR-2. [ABSTRACT FROM AUTHOR]

2‐Aminobenzothiazoles are widely used in the fields of pharmaceuticals and pesticides. Herein, we report a metal‐free protocol for the preparation of 2‐aminobenzothiazoles by a covalent organic framework (COF) catalyzed tandem reaction. In the presence of catalytic amount of phenanthroline‐decorated COF (Phen‐COF), a variety of 2‐aminobenzothiazoles are obtained in excellent yields by the cross‐coupling of 2‐iodoanilines with isothiocyanates at room temperature in water. In addition, the COF‐catalyst is very stable and can be reused at least seven times without loss of its catalytic activity. [ABSTRACT FROM AUTHOR]

An early exploration of the benzothiazole class against two kinetoplastid parasites, Leishmania infantum and Trypanosoma cruzi, has been performed after the identification of a benzothiazole derivative as a suitable antileishmanial initial hit. The first series of derivatives focused on the acyl fragment of its class, evaluating diverse linear and cyclic, alkyl and aromatic substituents, and identified two other potent compounds, the phenyl and cyclohexyl derivatives. Subsequently, new compounds were designed to assess the impact of the presence of diverse substituents on the benzothiazole ring or the replacement of the endocyclic sulfur by other heteroatoms. All compounds showed relatively low cytotoxicity, resulting in decent selectivity indexes for the most active compounds. Ultimately, the in vitro ADME properties of these compounds were assessed, revealing a satisfying water solubility, gastrointestinal permeability, despite their low metabolic stability and high lipophilicity. Consequently, compounds 5 and 6 were identified as promising hits for further hit‐to‐lead exploration within this benzothiazole class against L. infantum, thus providing promising starting points for the development of antileishmanial candidates. [ABSTRACT FROM AUTHOR]

Breast cancer, a deadly disease among women, demands effective interventions due to its global impact, with over one million annual cases. Current anti-breast cancer drugs displays several side effects, also most patients resists to these drugs during early treatment stage. Hence, global search for better drugs with less side effects became necessary. The objective of this study is to identify potential inhibitors of vascular endothelial growth factor receptor-2 (VEGFR-2), a critical target in breast cancer treatment. Molecular docking-based virtual screening of 45 benzoxazole/thiazole derivatives was conducted, followed by molecular dynamics simulations to explore ligandprotein interactions. Seven ligands (compounds 7, 10, 12, 13, 14, 20, and 26) demonstrated superior binding affinities ranging from -157.85 to -173.88 kcal/mol (MolDock scores) and -109.96 to -129.23 kcal/mol (Rerank scores) compared to Sorafenib (-156.35 kcal/mol MolDock score and -102.63 kcal/mol Re-rank score). Compound 7, identified as a potential hit, exhibited stability in a 100-ns dynamic simulation. It was chosen as a template for designing novel inhibitors, resulting in five compounds with improved binding affinities ranging from -177.84 to -184.69 kcal/mol (MolDock scores) and -137.34 to -143.44 kcal/mol (Re-rank scores). Pharmacological profiling confirmed the drug-like properties of both the potential hit molecules and the designed compounds, with 0-1 violations against Lipinski's rule of five and favorable pharmacokinetics status. Density functional theory (DFT) studies illustrated the reactive nature of the designed compounds. These findings suggest the potential of these molecules as novel VEGFR-2 inhibitors for breast cancer treatment, providing promising prospects for future drug development. [ABSTRACT FROM AUTHOR]

Introduction: Cancer, a significant global health concern, necessitates innovative treatments. The pivotal role of chronic inflammation in cancer development underscores the urgency for novel therapeutic strategies. Benzothiazole derivatives exhibit promise due to their distinctive structures and broad spectrum of biological effects. This study aims to explore new anti-tumor small molecule drugs that simultaneously anti-inflammatory and anticancer based on the advantages of benzothiazole frameworks. Methods: The compounds were characterized by nuclear magnetic resonance (NMR), liquid chromatograph-mass spectrometer (LC-MS) and high performance liquid chromatography (HPLC) for structure as well as purity and other related physicochemical properties. The effects of the compounds on the proliferation of human epidermoid carcinoma cell line (A431) and human non-small cell lung cancer cell lines (A549, H1299) were evaluated by MTT method. The effect of compounds on the expression levels of inflammatory factors IL-6 and TNF-α in mouse monocyte macrophages (RAW264.7) was assessed using enzyme-linked immunosorbent assay (ELISA). The effect of compounds on apoptosis and cell cycle of A431 and A549 cells was evaluated by flow cytometry. The effect of compounds on A431 and A549 cell migration was evaluated by scratch wound healing assay. The effect of compounds on protein expression levels in A431 and A549 cells was assessed by Western Blot assay. The physicochemical parameters, pharmacokinetic properties, toxicity and drug similarity of the active compound were predicted using Swiss ADME and admetSAR web servers. Results: Twenty-five novel benzothiazole compounds were designed and synthesized, with their structures confirmed through spectrogram verification. The active compound 6-chloro-N-(4-nitrobenzyl) benzo[d] thiazol-2-amine (compound B7) was screened through a series of bioactivity assessments, which significantly inhibited the proliferation of A431, A549 and H1299 cancer cells, decreased the activity of IL-6 and TNF-α, and hindered cell migration. In addition, at concentrations of 1,2, and 4 μM, B7 exhibited apoptosis-promoting and cell cycle-arresting effects similar to those of the lead compound 7-chloro-N-(2, 6- dichlorophenyl) benzo[d] thiazole-2-amine (compound 4i). Western blot analysis confirmed that B7 inhibited both AKT and ERK signaling pathways in A431 and A549 cells. The prediction results of ADMET indicated that B7 had good drug properties. Discussion: This study has innovatively developed a series of benzothiazole derivatives, with a focus on compound B7 due to its notable dual anticancer and anti-inflammatory activities. B7 stands out for its ability to significantly reduce cancer cell proliferation in A431, A549, and H1299 cell lines and lower the levels of inflammatory cytokines IL-6 and TNF-α. These results position B7B7 as a promising candidate for dual-action cancer therapy. The study's mechanistic exploration, highlighting B7's simultaneous inhibition of the AKT and ERK pathways, offers a novel strategy for addressing both the survival mechanisms of tumor cells and the inflammatory milieu facilitating cancer progression. [ABSTRACT FROM AUTHOR]

The nucleophilic substitution reactions of mono- and bis-spiro-2,2'-dioxybiphenyl cyclotriphosphazenes (1a and 1b) with 2-hydroxybenzothiazole (2) were performed in the presence of metallic sodium in THF. Two novel 2-oxybenzothiazole-substituted spiro-2,2′-dioxybiphenyl cyclotriphosphazene derivatives (3a and 3b) were obtained from these reactions. Both compounds (3a, 3b) have been characterized by elemental analysis as well as by 1H, 13C and 31P NMR spectroscopy. Compounds 3a and 3b are reported for the first time in this study. [ABSTRACT FROM AUTHOR]

Synthesis of imidazo[2,1‐b][1,3]benzothiazoles by oxidative coupling of 2‐aminobenzothiazoles with vicinal diol was reported. Expectedly, a combination of potassium persulfate and TEMPO oxidized ethylene glycol to α‐hydroxy acetaldehyde, which coupled with 2‐aminobenzothiazole to afford 2,3‐unsubstituted imidazo[2,1‐b][1,3]benzothiazoles. The later was exploited as a reliable handle to access 3‐substituted imidazo[2,1‐b][1,3]benzothiazoles regioselectively. [ABSTRACT FROM AUTHOR]

A novel hydroxy benzothiazole based yellow fluorescent powder (labelled as 2‐SiO2) was prepared by adsorption of 2 on silica (4 % w/w) for visualization of latent fingerprints (LFPs) and glove prints using powder dusting method. The solid‐state spectrum of 2‐SiO2 shows emission peak at 550 nm with CIE‐1931 coordinates (x,y ${x,y}$) of 0.42, 0.50 and yellow colour purity is 58.6 %. The high fluorescence of 2 in the solid‐state could be attributed to AIE+ESIPT features. Due to high fluorescence (ϕ=0.422) ${(\varphi{} =0.422)}$ of 2‐SiO2 (4 % w/w) powder, fluorescence imaging of LFPs on a variety of porous and non‐porous substrates including glove prints, up to levels 1–3, without any post‐treatment has been achieved. The 2‐SiO2 showed strong interaction with D‐Glucose, urea and lactate components present in sweat. The practical applications of 2‐SiO2 powder have been demonstrated by analysis of LFPs, development of LFPs at different temperatures; aged, stained fingerprints and preservation of developed fingerprints for documentation purposes. [ABSTRACT FROM AUTHOR]

Heteroarylphosphonium salts are easily accessible, versatile intermediates in functionalization of N‐heterocycles. Direct C−C bond formation by net substitution of the phosphine has so far required transition metal catalysts, the use of strongly basic reagents or redox catalysis. Here we describe a C−C bond formation in direct reactions of benzothiazol‐2‐yl‐phosphonium and pyridin‐4‐yl‐phosphonium salts and nitrile anions which, together with the direct synthesis of phosphonium salts from benzothiazoles and pyridines, constitutes an efficient and simple two‐step protocol for C−H functionalization of these heterocycles under mild conditions. [ABSTRACT FROM AUTHOR]

Dyes derived from benzothiazoles are an important class of heterocycles which have remarkable photophysical properties. New photoluminescent 2-phenylbenzothiazole derivatives containing different functional groups were synthesized in high yields and used for silylated derivatives synthesis. The new photoactive compounds were fully characterized and their photophysical properties were investigated. The absorption and fluorescence spectra of the benzothiazoles and their silylated derivatives were evaluated in a series of organic solvents. The results showed that the benzothiazoles present absorption in the ultraviolet range and emission in the blue region with moderate quantum yields and large Stokes shift. The solvatochromism of these compounds was investigated by using Lippert and ET(30) Dimroth-Reichardt empirical solvent polarity scales. The dipole moments obtained by Bakshiev and Kawaski-Chamma-Viallet equations revealed that the excited states were more polar than the ground states. [ABSTRACT FROM AUTHOR]

In the title compound, C12H11N3OS, the interplanar angle between the pyrazole and benzothiazole rings is 3.31 (7)°. In the three-dimensional molecular packing, the carbonyl oxygen acts as acceptor to four C--H donors (with one H…O as short as 2.25 Å), while one methyl hydrogen is part of the three-centre system H…(S, O). A double layer structure parallel to (...01) can be recognized as a subsection of the packing. [ABSTRACT FROM AUTHOR]

A novel porous metal–organic framework Co(btc)(bpy) (Co-MOF-3a) was synthesized by employing a bipyridyl ligand, benzene tricarboxylic acid, and Co(NO3)2·6H2O and was completely characterized. The mesoporous nature of the MOF catalyst was confirmed using BET measurements. The confirmation of the proposed structure of Co-MOF-3a was also supported through a computational study. This MOF could serve as a highly efficient heterogeneous catalyst for the oxidation of a variety of alcohols with tert-butyl hydroperoxide (t-BuOOH) as an oxidant. Furthermore, the current catalytic approach facilitated the oxidative coupling reaction in one pot to obtain a wide range of biologically important molecules, such as benzimidazole, benzothiazole, quinozolones, and arylidene malononitrile. The high performance of the MOF could be due to the presence of both the metal and carboxylate group of the ligand. The recyclability and scalability of the catalyst was found to be efficient and suitable for commercial applications. [ABSTRACT FROM AUTHOR]

Triarylhydrazones represent an attractive class of photochromic compounds offering many interesting features including high molar absorptivity, good addressability, and extraordinary thermal stability. In addition, unlike most other hydrazone‐based photoswitches, they effectively absorb light above 365 nm. However, previously prepared triaryhydrazones suffer from low quantum yields of the Z→E photoisomerization. Here, we have designed a new subclass of naphthoyl‐benzothiazole hydrazones that balance the most beneficial features of previously reported naphthoyl‐quinoline and benzoyl‐pyridine triarylhydrazones. These preserve the attractive absorption characteristics, exhibit higher thermal stability of the metastable form than the former and enhance the rate of the Z→E photoisomerization compared to the later, as a result of the weakening of the intramolecular hydrogen bonding between the hydrazone hydrogen and the benzothiazole moiety. Introducing the benzothiazole motif extends the tunability of the photochromic behaviour of hydrazone‐based switches. [ABSTRACT FROM AUTHOR]

Heterocycles, compounds featuring heteroatoms like nitrogen, sulfur, and oxygen, are integral in fields such as synthesis, pharmacology, and medicine. Among these, benzothiazoles, formed by fusing thiazole with benzene, hold significant prominence. Their unique reactivity, especially at the carbon position between nitrogen and sulfur, has sparked wide interest. Notably, 2-substituted benzothiazoles exhibit diverse biological activities, including anticonvulsant, antimicrobial, and antioxidant properties, making them valuable in drug discovery. This review unveils an array of mesmerizing methods employed by chemists to prepare these compounds using 2-aminothiophenol as one of the precursors with other varied reactants. From novel strategies to sophisticated methodologies, each section of this review provides a glimpse into the fascinating world of synthetic chemistry of 2-substituted benzothiazoles. Delving into the diverse synthetic applications of 2-substituted benzothiazoles, this paper not only enriches our understanding of their synthesis but also sparks the imagination with the possibilities for future advancements. [ABSTRACT FROM AUTHOR]

Nuclear energy holds the chief portion of the global primary energy mix that comes with the major issue of releasing volatile nuclear wastes viz. radioiodine (129I and 131I) into air and water bodies during nuclear fuel reprocessing. The efficient capture of volatile radioiodine has attracted a major attention worldwide due to the severe health and environment effects. Among various porous materials, covalent organic frameworks (COFs) are the intriguing class of porous organic materials with crystallinity, synthetically pre-designable functionalities to achieve tunable properties. Herein, a new benzothiazole based COF (COF-3) obtained by the condensation of 2,6-dimainobenzothiazole and 2,4,6-triformylpholoroglucinol is reported with tetragonal pore topology (pore volume = 0.305 cc g−1; BET surface area = 57.9 m2 g−1). The electron rich heteroatoms in the frameworks play a crucial role in adsorbing electron deficient iodine molecules and therefore, the benzothiazole-derived COF is envisioned to be potent material for efficient iodine adsorption. The synthesized COF showed the iodine adsorption capacity of 1.07 g g−1 in vapor phase and 109.0 mg g−1 from n-hexane solution. A reference COF (COF-4) with no thiazole group derived from 1,4-phenylenediamine and 2,4,6-triformylpholoroglucinol with hexagonal pore topology (pore volume = 0.937 cc g−1) and BET surface area 133.9 m2 g−1 showed adsorption of iodine from n-hexane solution with capacity 149.5 mg g−1. The study revealed that although the presence of heteroatoms in the framework facilitates the iodine adsorption by converting the molecular iodine into the polyiodides; the factors such as BET surface area, pore topology and pore volume also play a major role in the adsorption of iodine molecules. [ABSTRACT FROM AUTHOR]

Sustainability is one of the hot topics of today's research, in particular when it comes to energy‐storage systems such as batteries. Redox‐active molecules implemented in organic batteries represent a promising alternative to lithium‐ion batteries, which partially rely on non‐sustainable heavy metal salts. As an alternative, we propose benzothiazole, ‐oxazole and ‐imidazole derivatives as redox‐active moieties for polymers in organic (radical) batteries. The target molecules were identified by a combination of theoretical and experimental approaches for the investigation of new organic active materials. Herein, we present the synthesis, electrochemical characterization and theoretical investigation of the proposed molecules, which can later be introduced into a polymer backbone and used in organic polymer batteries. [ABSTRACT FROM AUTHOR]

The article discusses the use of benzoxazole and benzothiazole as directing groups for palladium- and ruthenium-catalyzed C-H arylation reactions. The authors explore different reaction conditions and catalysts to achieve selective arylation of these compounds. They also investigate the effects of substituents on the aryl unit and the benzoxazole/benzothiazole moiety. The document provides valuable information for researchers interested in the synthesis and functionalization of heterocyclic compounds. Additionally, the document includes experimental procedures and characterization data for specific compounds synthesized using the methods discussed. [Extracted from the article]

The use of ligand combination approach in the Pd catalyzed direct C−H arylation of benzothiazole and benzoxazole is demonstrated. The combination of two ligands phenanthroline monohydrate (Phen.H2O) and triphenylphosphine (PPh3) with Pd‐catalyst have offered the best catalytic properties in the C−H bond arylation reactions than either of two ligands employed separately in the reactions. This protocol exhibits a wide substrate scope affording C2 arylated benzothiazole and benzoxazole derivatives in excellent yields. Mechanistic studies including kinetic isotope effect (KIE), H/D exchange and competition experiments show that the C−H bond activation of benzothiazole and benzoxazole is very facile under reaction conditions. Furthermore, different mechanistic pathways originated from the catalytically active species such as Pd(η2‐dba)L (dba=dibenzylidene acetone) and Pd(PPh3)2 were investigated using computational methods. The computational results suggest that the generation of catalytically active species from Pd2(dba)3 is endoergic process and Phen ligand can initiate this step. On the other hand, the presence of PPh3 could be crucial for the oxidative addition of aryl halides which is the rate‐determining step of the reaction. [ABSTRACT FROM AUTHOR]

The excited state relaxation dynamics of 2-(2′-hydroxyphenyl)benzothiazole (HBT) in the gas phase and the solvents have been explored experimentally and theoretically. However, the fundamental mechanism of its emission in aggregates is still unexplored. In this article, we have presented a detail investigation of solvent-regulated excited state (ES) reactions for HBT aggregates with the aid of several experimental and theoretical research. The careful investigation of solvatochromic and electrochemical behavior elucidates that the emission around 460 nm of HBT in DMSO and DMSO–water fraction correspond to the excited state internal charge transfer (ESICT). The quantum chemical analysis further supports this observation. The concentration-dependent 1H NMR and emission studies of HBT in DMSO revealed the formation of aggregates at higher concentrations that facilitate the charge transfer. The emission pattern of HBT in the AcN–water fraction demonstrates that the sequential internal charge transfer-proton transfer (ESICT–ESIPT) occurs in HBT aggregates. The pH studies show that HBT aggregates are potential ratiometric sensors for near-physiological pH ranges. Moreover, a ground-state zwitterionic conformation of HBT is observed in the basic medium formed by ground-state internal proton transfer (GSIPT). Overall, this study provides a better understanding of solvent-regulated ES reaction mechanism in the case of HBT aggregates and other substituted HBT compound aggregates published previously. [ABSTRACT FROM AUTHOR]

This paper is focused on the optimalization of methods for the synthesis, isolation, and purification of 2-mercaptobenzothiazole-based acrylic and methacrylic monomers. The structures of the newly synthesized compounds were confirmed through infrared (IR) and nuclear magnetic resonance spectroscopy (NMR). Spectroscopic properties of the resulting 2-mercaptobenzothiazole derivatives were determined based on their absorption spectra and molar absorption coefficients in solvents with varying polarities. A correlation was established between the calculated density functional theory (DFT) energies and Frontier Molecular Orbitals and the experimental observations, confirming their consistency. The practical utility of the synthesized compounds, particularly in future polymerization processes, hinges on a thorough understanding of these properties. [ABSTRACT FROM AUTHOR]

Ag electrode is widely used in inverted perovskite solar cells (PSCs), but its easy reaction and corrosive nature with perovskite always induces severe stability issue. Here, from typical theory of metal anticorrosion, a chemical anticorrosion approach for Ag electrode in inverted PSCs through introducing 2‐mercaptobenzothiazole (MBT) as a corrosion inhibitor is reported. MBT can strongly bond to Ag and form a compact [MBT‐Ag] chain on Ag surface owing to its N atom in thiazolyl ring and exocyclic thiol groups. As a result, Ag anticorrosion ability is greatly enhanced by increasing the corrosion potential and decreasing the corrosion current, thus effectively inhibiting possible chemical reaction and corrosion between perovskite and Ag electrodes. PSCs containing MBT/Ag exhibit high efficiency of over 23% with good stability, retaining 95 ± 4.1% of initial efficiency after storage for 3800 h in glovebox. Importantly, resulting PSCs also show excellent thermal stability, maintaining 90 ± 1.8% of initial efficiency after aging for 900 h at 85 °C. [ABSTRACT FROM AUTHOR]

Benzimidazole (BNIMZ) and benzothiazole (BNTZA) based compounds are studied to understand their binding features with poly-A.poly-T DNA sequence and their mode of binding is also explored. According to thermal denaturation data, BNTZA slightly favors DNA stability with a 2.9°C advantage over BNIMZ. The DNA conformational stability of the BDNA form was recorded with and without ligands by circular dichroism. The estimated docking scores support the findings from the UV denaturation investigation, and we observed that BNTZA had a higher docking score than BNIMZ. With the help of 50 ns MD simulations, additional conformational analyses have been performed. Both compounds effectively bind to the minor-grooves of AT-rich DNA sequence with a favorable binding free energy in accordance with the RMSD analysis, and pucker distribution of deoxyribose sugars. Future oligonucleotide therapies may be benefited because of the current discovery. [ABSTRACT FROM AUTHOR]

Lipid droplets are essential for cellular lipid storage, playing critical roles in cellular lipid metabolism. Although lipid droplets have drawn intense research in recent years, much remains to be uncovered about the roles of this organelle in biology. Lipid droplet indicators exhibiting large Stokes shifts and improved brightness are therefore in demand. We report two asymmetric BODIPY derivatives, BoL1 and BoL2 bearing a benzothiazole group at the 6‐position, which led to bathochromic shifts of 62 nm for BoL1 and 37 nm for BoL2 in fluorescence emission when compared to the reference molecules without the benzothiazole group. The incorporation of the benzothiazole moiety also resulted in a large Stokes shift of 40 nm. BoL1 and BoL2 have been demonstrated to operate as lipid droplet indicators in both confocal and STED imaging. BoL2 showed particularly good cellular retention and was further applied to explore the impact of cellular starvation on the trafficking of lipid droplets. [ABSTRACT FROM AUTHOR]

In this study, new 1,3-thiazolidin-4-one derivatives containing arylmethylene groups in the 5-position were obtained from 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine (riluzole). Synthesized compounds were characterized by spectral data and elemental analysis. In vitro, cytotoxic activities of the synthesized molecules were evaluated against the human lung cancer (A549) and human prostate cancer (PC-3) cell lines. Compounds were also tested on mouse embryonic fibroblast cells (NIH/3T3) to determine selectivity. Ten target compounds 3-12 were also screened for their COX-1 and COX-2 inhibitory activities. Of these compounds, 4 showed the highest COX-2 inhibition at 10 μM. Molecular docking calculations were performed to understand the binding interactions of compounds with COX-1 and COX-2 proteins. In silico studies of the tested compounds represented important binding modes that may be responsible for their anti-cancer activity via selective inhibition of the COX-2 enzyme. ADMET predictions were conducted to assess the drug-like properties of the novel compounds. [ABSTRACT FROM AUTHOR]

We report herein an efficient synthesis of 3‐arylbenzothiazolin‐2‐one compounds. First, substituted benzothiazoles can be smoothly oxidized to benzothiazolin‐2‐one derivatives in the presence of CuCl2 and trifluoroacetic anhydride. Secondly, the Cu2S‐catalyzed N‐arylation of benzothiazolin‐2‐one with arylboronic acids yields a series of novel 3‐aryl benzothiazolin‐2‐one derivatives. The method provides good yields for a variety of substrates and shows good compatibility with functional groups. The usefulness of the skeleton was further illustrated by the derivatization of 3‐aryl‐benzothiazolin‐2‐one. Mechanistic studies suggest that the oxidation of benzothiazole may undergo a free radical reaction process. [ABSTRACT FROM AUTHOR]

Antimitotic agents are one of the more successful types of anticancer drugs, but they suffer from toxicity and resistance. The application of approved drugs to new indications (i.e., drug repurposing) is a promising strategy for the development of new drugs. It relies on finding pattern similarities: drug effects to other drugs or conditions, similar toxicities, or structural similarity. Here, we recursively searched a database of approved drugs for structural similarity to several antimitotic agents binding to a specific site of tubulin, with the expectation of finding structures that could fit in it. These searches repeatedly retrieved frentizole, an approved nontoxic anti-inflammatory drug, thus indicating that it might behave as an antimitotic drug devoid of the undesired toxic effects. We also show that the usual repurposing approach to searching for targets of frentizole failed in most cases to find such a relationship. We synthesized frentizole and a series of analogs to assay them as antimitotic agents and found antiproliferative activity against HeLa tumor cells, inhibition of microtubule formation within cells, and arrest at the G2/M phases of the cell cycle, phenotypes that agree with binding to tubulin as the mechanism of action. The docking studies suggest binding at the colchicine site in different modes. These results support the repurposing of frentizole for cancer treatment, especially for glioblastoma. [ABSTRACT FROM AUTHOR]

Driven by the growing threat of cancer, many research efforts are directed at developing new chemotherapeutic agents, where the central role is played by transition metal complexes. The proper ligand design serves as a key factor to unlock the anticancer potential of a particular metal center. Following a recent trend, we have prepared unsymmetrical pincer ligands that combine benzothiazole and thiocarbamate donor groups. These compounds are shown to readily undergo direct cyclopalladation, affording the target S,C,N-type Pd(II) pincer complexes both in solution and in the absence of a solvent. The solid-phase strategy provided the complexes in an efficient and ecologically friendly manner. The resulting palladacycles are fully characterized using nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy and, in one case, by single-crystal X-ray diffraction (XRD). The solvent-free reactions are additionally analyzed by powder XRD. The pincer complexes exhibit remarkable cytotoxicity against several solid and blood cancer cell lines, including human colorectal carcinoma (HCT116), breast cancer (MCF7), prostate adenocarcinoma (PC3), chronic myelogenous leukemia (K562), multiple plasmacytoma (AMO1), and acute lymphoblastic leukemia (H9), with the dimethylamino-substituted derivative being particularly effective. The latter also induced an appreciable level of apoptosis in both parental and doxorubicin-resistant cells K562 and K562/iS9, vindicating the high anticancer potential of this type of palladacycles. [ABSTRACT FROM AUTHOR]

In the present study a series of ethyl 4-(substituted)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate and ethyl 4-(substituted)-8-methoxy-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate have been synthesized and evaluated for their preliminary antibacterial, antifungal, antimycobacterial, antioxidant and antimalarial activity. Among all the synthesized derivatives some of the compounds exists good biological activity which is similar to that of standard drugs. These facts make the compounds interesting candidates for further evaluation of their efficacy in the treatment microbial, tubercular and malarial disease. [ABSTRACT FROM AUTHOR]

Fifteen compounds containing benzothiazole have been synthesized successfully via Suzuki reaction of 2-(4-bromophenyl)benzothiazole 1 and phenylboronic acid derivatives in high yield. All samples display fluorescence emissions at wavelengths in the range of 380 to 450 nm under the excitation light of 330 nm. Compounds 2d, 2e, 2h and 2k exhibit quite good fluorescent property. [ABSTRACT FROM AUTHOR]