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In the current scenario we have plant to study to synthesize novel indole derivatives (4a-d) and (5a-b) which have the target activity like anti-convulsion and anti microbial etc. In the primary phase, we synthesized 2-phenyl-1H-indole reacted with Phosphorus oxychloride and N, N’-dimethylformamide by using vilsmeier reagent formylation of a new compound 2-phenylindole-3-carbaldehyde (2). The 2-phenylindole-3-carbaldehyde was reacted with substituted phenacyl bromide, K2CO3 and TBAB (Tetra butyl ammonium bromide) into the presence of N, N’-dimethylformamide to gives [1-(2-(4-substituted phenacyl bromide)-2-oxoethyl)-2-phenylindole-3-carbaldehyde (3a-d). The compound [1-(2-(4- substituted phenacyl bromide)-2-oxo-ethyl)-2-phenylindole-3-carbaldehyde was permitted to mixed with various substituted phenacyl bromide gives corresponding indole derivatives. The indole derivatives (3a-d) were reacted with barbituric acid and thiobarbituric acid dissolved into the methanol at reflux for 4h to gives afforded compounds (4a-d) and (5a-b). The final indole barbituric derivatives (4a-d) and (5a-b) were synthesized from substituted phenacyl bromide by the react with methanol and recrystalized from ethanol. The last compound has been completed on the basis of spectra FT-IR and 1H NMR. All the value of FT-IR, 1H NMR, Solubility and TLC were considered to be prominent. The pharmacological screening through ear electrode induced current 50mA for 0.2 seconds in electro-convulsiometer for anticonvulsant activity. The synthesize compounds were establish to be 4b, 4c, 4d, and 5a. The compound 4c and 5a were established to be the most potent compound through compare to standard drugs phenytoin sodium.

Herein, a convenient and efficient synthesis of 7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives was achieved from the reaction of isoquinolinium N-ylides, aromatic aldehydes, and heterocyclic 1,3-dicarbonyl compounds via one-pot three-component diastereoselective domino reaction in good-to-excellent yields. The advantages of this protocol are easily available starting materials, operational simplicity, and avoidance of hazardous organic solvents and catalyst. The synthesized products were characterized by IR, 1H NMR, 13C NMR and mass spectra. Additionally, the conclusive structure of target compounds was confirmed by X-Ray diffraction analysis.

The concept of a green approach has been applied in the reaction, separation and solidification of a single unit. The products, 2-benzimidazol-diphenyl-2-imino-thiazolidine-4-ols, are purely hemiaminals. They have a tendency to decompose at a high rate. The solid-phase reactive chromatographic technique has been applied to avoid extensive liquid–liquid extraction and stabilised the product by precipitation in solvents. Benzimidazole phenyl thiourea and phenacyl bromide have been used as starting materials in this study. Both the starting materials are adsorbed on dry silica and packed in a glass column with a systematic arrangement of layers. A directly solid product was precipitated in cold hexane. Anticancer activities have been recorded against four cell lines, human colon, prostate, lung and breast cancer, with reference to doxorubicin as a standard. These compounds show a promising effect on human lung cancer, products B9 (IC50 = 3.890 μM) and B10 (IC50 = 2.798 μM) and B13 (IC50 = 3.140 μM) which very close to doxorubicine (IC50 = 1.750 μM). It was observed that fluoro phenyl functionalities are effective compared to trifluoro methyl phenyl functionalities for anticancer activities. These small molecules lose their activities, except fluorination, on bulky substitution. This convenient metal-free approach is highly efficient for unstable hemiaminals such as the potent anticancer benzimidazol-diphenyl-2-imino-thiazolidine-4-ols.

A metal-free, simultaneous triple C-C coupling cyclization reaction between phenacyl bromides and indoles is discovered in a highly regioselective fashion to furnish 3,5-diarylcarbazoles. DMAP is utilized as the only reagent for the unusual and rapid cyclization reaction to furnish all new carbazole compounds through installation of a great diversity of substituents. A plausible radical mechanism for the new reaction is predicted by conducting various control experiments, competitive reactions, furoindole formation, and ESI-MS analyses of the ongoing cyclization reaction.

The synthesis of previously unknown unsaturated aromatic oxyethers was carried out by reaction of chloromethylpropargyl(allyl) ether with phenacyl bromide, with the participation of the chiral catalyst - (+)-benzotetramisole, and their configurations were also established. It was shown the anisotropic effect of the phenyl group in the acid chloride of α-methoxytrifluoromethylphenylacetic acid (MTPA-Cl) on the halogenaryl group. Such effect leads to screening of the latter, and this, in turn, leads to a shift to a strong field and positive values of ∆δR/S, while proton signals of the less bulky group are shifted to a weaker field with a negative value of ∆δR/S. The interaction of chloromethylpropargyl (allyl) ether with phenacylbromide with the participation of the chiral catalyst - (+) - benzotetramisole leads to aromatic allyl and propargyl alcohol monoethers. By the chiral derivative agent (CDA) chloride anhydride- α-trifluoro-methyl-phenyl-acetic acid (MTPA-Cl) the absolute configuration of compounds was determined. Due to comparing the ΔδR/S data in the NMR 1H spectra during such interaction it was found that they converted to diastereomers.

An efficient and atom economic modification of a previously reported synthetic pathway to tetrasubstituted thiophenes is described. The previously published synthetic methodology involved a one pot procedure starting with ketene dithioacetal and an appropriate secondary amine, and subsequent reaction with Na2S and phenacyl bromide. However, the liberated methanethiolate by-product was competed with enethiolate intermediate for phenacyl bromide, which reduced the yield and imposed the necessity to use two molar equivalents of α-haloketone reagent to increase the yield of the target thiophene products. In the present work, the proposed modification consisted in isolation of the intermediate enethiolate derivative, thereby reducing quantity of the α-haloketone to one molar equivalent. Moreover, the reaction conditions were optimized to attain optimum base/solvent combination to improve the yield of the target derivatives. Following our modified procedure, three series of new 3-amino-4-cyanothiophene derivatives were synthesized and isolated in high yields and high purity.

A new set of thiazolyl-pyrazolines 3a–l was prepared by cyclization of carbothioamides 2a–g with phenacyl bromide and/or 4-bromo phenacyl bromide. The new chemical entities were tested for their antimicrobial properties, while none of the tested samples showed promising activity. The derivatives 2a–c demonstrated moderate potency against Staphylococcus aureus having the potential to be optimized into promising antimicrobial candidates. In addition to elemental analyses, the structural elucidation of the new analogues was carried out via IR, 1H NMR, 13C NMR as well as mass spectral data.

COVID-19 is a global pandemic caused by infection with the SARS-CoV-2 virus. Remdesivir, a SARS-CoV-2 RNA polymerase inhibitor, is the only drug to have received widespread approval for treatment of COVID-19. The SARS-CoV-2 main protease enzyme (MPro), essential for viral replication and transcription, remains an active target in the search for new treatments. In this study, the ability of novel thiazolyl-indazole derivatives to inhibit MPro is evaluated. These compounds were synthesized via the heterocyclization of phenacyl bromide with (R)-carvone and (R)-pulegone thiosemicarbazones. The binding affinity and atomistic interactions of each compound were evaluated through Schrödinger Glide docking, AMBER molecular dynamics simulations, and MM-GBSA free energy estimation, and these results were compared with similar calculations of MPro binding various 5-mer substrates (VKLQA, VKLQS, VKLQG). From these simulations, we can see that binding is driven by residue specific interactions such as π-stacking with His41, and S/π interactions with Met49 and Met165. The compounds were also experimentally evaluated in a MPro biochemical assay and the most potent compound containing a phenylthiazole moiety inhibited protease activity with an IC50 of 92.9 µM. This suggests that the phenylthiazole scaffold is a promising candidate for the development of future MPro inhibitors.

Utility of 4-oxo-6-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 1 in synthesis of a new series of fused pyrimidines was described. Pyrimido[2,1-b][1,3]thiazines 6–9 were obtained via Michael addition of compound 1 to the polarized systems 2–5 in the presence of nanosized ZnO. S-alkylation of pyrimidine 1 followed by cyclization with phenacyl bromide, monochloroacetic acid, chloroacetonitrile and oxalyl chloride afforded the desired thiazolo[3,2-a]pyrimidines 10–13. Hydrazinolysis of compound 1 followed by addition cyclization with acetic anhydride, formic acid, carbon disulfide and benzoyl chloride afforded triazolo[4,3-a]pyrimidines 15–18. The antimicrobial screening showed high activity for thiazolo[3,2-a]pyrimidines 11 and 12 against both Gram (+ ve) and Gram (− ve) bacteria.

Visible-light active, heterogeneous, and organic photocatalysts exhibit a more sustainable and environmentally friendly alternative to classical metal-based catalysts. Two-dimensional covalent organic frameworks (2D-COFs) with permanent porosity, columnar π-arrays and excellent stability, that can become an excellent platform for heterogeneous photocatalysis of organic transformations. Here we report a predesigned imine-based COF with electron donor and acceptor structure. And new framework possesses large surface area, high crystallinity, outstanding stability and broad absorption range in the visible-light region as well as good photoelectric response characteristics. Importantly, it was found to be a highly effective heterogeneous photocatalyst for reductive dehalogenation of phenacyl bromide derivatives and α-alkylation of aldehydes under irradiation of visible-light. In addition, the COF gave good recyclability and could be reused after a simple separation manipulation. The current present still reveals a great prospect for 2D-COFs as metal-free, heterogeneous photocatalysts for organic transformations.

Copper nanoparticles as an efficient, inexpensive catalyst were prepared via ball milling for synthesis of β-carbonyl 1, 2, 3-triazoles from azido alcohol by click reaction in water. An extensive range of raw materials such as sodium azide, phenacyl bromide, epichlorohydrin, and terminal alkynes were used. Complete reduction of CuO in presence of NaBH4 was done via ball milling with a ball-to-powder weight ratio of 50:1 under air atmosphere at room temperature. The final copper nanoparticles (Cu NPs) were characterized by SEM, EDX, XRD and FT-IR. The Cu NPs catalyzed one-pot three component synthesis of β-carbonyl 1, 2, 3-triazoles at room temperature with short reaction time and high product yields. The catalyst could be easily recovered and reused in several successive runs.

In this study, the synthesis of new spiropyrazoles, pyrazole and hydantoin heterocycles is reported by three component reactions of parabanic acids, hydrazine derivatives, and phenacyl bromides in the presence of triphenylphosphine as a nucleophile and triethylamine as a base in good to high yields (69-91 %). Evaluation of the synthesized compounds revealed a good to excellent antioxidant activities (37.6-96.2 %) using DPPH inhibitory potency. Among these compounds, hydantoin derivatives displayed higher antioxidant activities (93.7-96.2 %) comparing with spiropyrazoles and pyrazoles. The obtained results showed that Cl and Br substituents on the phenyl ring increased antioxidant activities of the related heterocycles. The antibacterial activities of the synthesized compounds were examined against two Gram-negative (Escherichia coli and Pseudomonas aeruginosa) and two Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacteria. Among the synthesized heterocycles, 2-[1,3-dimethyl-2,5-dioxo-4-(2-oxo-2-phenylethyl)imidazolidin-4-yl]hydrazine-1-carbothioamide exhibited the excellent antibacterial activity against both Gram-positive and Gram-negative bacteria.

A novel mixed phosphonium–iodonium ylide was synthesized by alkylation of 5-phenyl-5H-dibenzophosphole with phenacyl bromide followed by deprotonation and oxidation of the resulting phosphonium ylide with (diacetoxyiodo)- benzene. The influence of the cyclic nature of the phosphonium moiety on the dynamic E/Z isomerism in the mixed ylide is discussed.

Revised Abstract A series of novel bi-thiazoles was synthesized by reaction of 2-(1-(2-(2-(1-(4-fluorophenyl)ethylidene)hydrazinyl)-4-methylthiazol-5-yl)ethylidene) hydrazine-1-carbothioamide 3 with a variety of hydrazonoyl chloride derivatives 4a-d, and 7 a-d affording 6a-d and 9a-d respectively in dioxane in the presence of triethyl amine as a base. Also, hydrazine-1-carbothioamide 3 reacts with substituted phenacyl bromide derivatives 10 a-d yielding 12a-d in appropriate reaction conditions. The mechanisms of the titled reactions were discussed. Structural assignments were based on spectroscopic methods (NMR, FTIR, MS). The new compounds were tested in vitro for their were subjected to in vitro anticancer screening against human hepatocellular carcinoma (HCT-116), (HepG-2) and the results showed that compounds 6a, 6d, 9a, 9c and 12a have promising activities compared with cisplatin reference drug.

Different novel 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazines and 1,2,4-triazolo[4,3-b][1,2,4]triazines have been obtained from heterocyclization of 3-substituted-4-amino-5-substituted-amino-1,2,4-triazoles (3a-d) and 3-substituted-4-amino-5-hydrazino-1,2,4-triazoles (9a,b) with (α and β) bifunctional compounds like chloromethyl biphenyl-phosphanoxide, pyruvic acid, phenacyl bromide, diethyl oxalate, triethyl orthoformate, triethyl phosphite, fluorinated benzaldehydes, carbon disulfide and ethyl chloroformate under different experimental settings. Fourier transformer infrared analysis (FTIR), Proton nuclear magnetic resonance (1H NMR) and 13C nuclear magnetic resonance (13C NMR), as well as that of the mass spectral data, were used as the appropriate characterization techniques for the chemical structures of all newly synthesized compounds. The newly prepared compounds were examined as an anti-inflammatory, antibacterial agents (against E. coli (Escherichia coli) and P. aeruginosa (Pseudomonas aeruginosa) as examples for Gram-negative bacteria and S. aureus (Staphylococcus aureus) as examples for Gram-positive bacteria), as well as antifungal (against C. albicans (Candida albicans)) agents. The newly prepared compound showed high antibacterial, antifungal, and anti-inflammatory activities in comparing with the commercial antibiotics Indomethacin, Nalidixic acid, Imipenem, and Nystatin. Docking of the most active compounds was performed depending on the results of antibacterial screening and the anti-inflammatory assay.

An easy access to a series of N-phenylmorpholine derivatives linked with thiazole or formazan moieties were achieved using simple experimental procedure under conventional and microwaves irradiation conditions. The reaction of 2-(N-phenylmorpholine)ethylidene)hydrazine-1-carbothioamide derivatives and [1-(4-morpholin-4-yl-phenyl)-ethylidene]-hydrazine with a variety of hydrazonoyl chlorides or phenacyl bromide derivatives afforded the corresponding thiazoles or N-substitutedhydrazino-derivatives linked to N-phenylmorpholine moiety in good to excellent yields. The structures of the newly synthesized compounds were fully emphasized and characterized by spectroscopic as well as elemental analyses. The mode of binding of some selected compounds with SS-DNA was evaluated using UV–Vis absorption, and viscosity measurements. The results showed intercalation binding mode of most of the tested compounds. Both antimicrobial and anti-cancer activities have been studied for some selected compounds from synthetic derivatives. Their results showed a remarkable efficacy for some derivatives against both examined microbes and cancer cells.

The highly substituted 1,2,4-trisubtituted imidazole was regioselectively synthesized via base mediated domino reaction of amidine scaffold with phenacyl bromide followed by in situ N-alkylation of imidazole. The reaction conditions were optimized in order to access three phenomenon (neutralization, condensation, and N-alkylation) in a single pot. A mechanism for the formation of N–H imidazole and its subsequent N-alkylation is depicted by isolation of reaction of intermediates. Electron donating group facilitate N-alkylation, whereas no N-alkylation was observed in the presence of electron withdrawing (NO2) group. The synthesized compounds and reaction intermediate were characterized using NMR, FTIR, and HRMS. Exact orientation of various aromatic rings in regioselective N-alkylated product was confirmed using single crystal X-ray analysis.

The research was aimed to synthesize heterocyclic derivatives containing thiazole fused p-hydroxybenzohydazide for antimycobacterial activity. As, literature survey reveals various substitutions on thiazole fused p-hydroxybenzohydazide moiety show a variety of remarkable activities, the new derivatives of thiazole fused p-hydroxybenzohydazide was prepared by using various substitutions on R and R’ positions. Considering various pharmacological activities the present work is designed to club thiazole fused p-hydroxybenzohydazide moiety with different phenacyl bromide and isothiocynate moieties. Synthetic studies started with reaction of p-hydroxymethylbenzoate (1) which on amination with hydrazine hydrate leads to form common intermediate p-hydroxybenzohydrazide (2). This intermediate (2) when undergoes nucleophilic addition reaction with aryl isothiocyanates were resulted in the formation of thiosemicarbazides (III.a-III.d). The cyclization reaction (step-III) was carried out by using different phenacyl bromides, actual cyclization takes place by using sodium acetate. Step-III was resulted in the formation of final compounds (IV.a-IV.h). All synthesized compounds were further characterized by melting point. The compounds showed single spot in TLC which assured the completion of reactions and the purity of the compounds. The compounds were synthesized by appropriate synthetic route. The melting points of compounds were determined. The melting points of compounds were determined and were uncorrected. Thin layer chromatography was carried out by using suitable solvent system selected on the basis of solubility and polarity. The Rf value was determined. All the newly synthesized compounds were subjected for characterization by Rotational and Vibrational spectra (IR), Nuclear Magnetic Resonance (NMR), Mass spectroscopy (MS) and C, H, N analysis. The newly synthesized by compounds were screened for antimycobacterial activity by radiometric method.

An efficient synthesis of 3-phenyl-1-(6-phenyl-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1H-pyrazol-5-amines was accomplished by a simple, atom-economical, and multicomponent approach. Reac...

The development of highly efficient and rapid photoinitiating systems for free radical photopolymerization under the irradiation of visible light has attracted increasing attention due to their widespread potential applications in, for example, 3D printing or dental polymers. Unfortunately, currently available visible-light-sensitive photoinitiators are not efficient enough for 3D printing applications suffering from low printing speeds. Here we describe a series of photoinitiating systems consisting of disubstituted aminoanthraquinone derivatives (i.e., 1-amino-4-hydroxyanthraquinone, 1,4-diaminoanthraquinone, and 1,5-diaminoanthraquinone) and various additives (e.g., tertiary amine and phenacyl bromide) toward the free radical photopolymerization of various acrylate monomers (such as commercial 3D resin) under the irradiation of blue to red LEDs. It is shown that the type and position of substituents of the aminoanthraquinone derivative can significantly affect its photoinitiation properties. The most e...

New series of 3-substituted heterocyclic compounds containing bridge head nitrogen were synthesized through multi-step reactions. In order to prepare the starting 2-substituted heterocyclic compounds of pyridine, a known procedure was used by condensation of 2-amino pyridine with (4-bromo phenacyl bromide). Carbaldehyde group was introduced at position-3 of prepared 2-substituted imidazo / pyridine rings by Vilsmeier-Haack reaction. 3-Carbaldehyde derivatives underwent Claisen condensation with different aryl ketons to give unsaturated ketones of these derivatives, which on cyclization with urea and thiourea afforded 3-cyclic oxopyrimidines and thiopyrimidines derivatives of imidazo / pyridine rings. In addition, 3-carbaldehyde derivatives was reacted with hydrazine, semicarbazide and hydroxyl amine hydrochloride to yield new hydrazone, semicarbazone and oxime derivatives of imidazo / pyridine rings. All prepared compounds were characterised via FT-IR spectroscopy, some of them were characterised by 1H-NMR spectroscopy. These new 3-subistituted derivatives of imidazo /pyridine rings were tested in different species bacterial and fungi. Some of tested compounds showed strong activity while the other showed moderate against. Interestingly, All these new prepared compounds showed high activity against fungi.

An efficient synthesis of 6-(2-chloro-4-fluorophenyl)-9-phenylimidazo[1,2-a][1,8]naphthyridine derivatives by the reaction of phenacyl bromide with substituted heterocyclic amines in the presence of DABCO catalyst is described. Solid state conditions of the process accelerate accumulation of the targeted products with high yields and exclude formation of side-products. Antibacterial and fungal activities tests of all newly synthesized products demonstrate their pronounced potency, which is the highest for compounds 5c–5e. Molecular docking studies support well with the antimicrobial activity data accumulated for the products.

Phenacyl bromides are used as a building blocks in synthetic organic chemistry, which serves as a key model for the development of various biologically important heterocyclic compounds and other in...

A greener approach for the synthesis of 4-oxo-4,5,6,7-tetrahydro indole derivatives has been achieved through Wang-OSO3H-mediated three-component reaction involving dimedone, phenacyl bromide, and ...

The objective of this study is to test In Vitro the twenty chemical compounds that contains Schiff base or oxazepine, indoline, imidazolo units in concentrations( 50, 100, 150) mg / dl as antifungal activity, against three pathogenic Candida species that occur in humans. We tested one isolates of ) Candida albicans ,Candida glabrata and Candida krusei). All these species affect human health . The study was carried out in the Laboratory of Public Health , directly of health for the period from May 2016 to April 2017 , Candida spp isolates used in this study were collected from patients admitted at some private clinical in Kirkuk city . All isolates were identified using CHROM agar and stored at -70 0C. Preparation of Schiff base ( 1-7 ) from amino pyridine derivatives with aromatic aldehyde by nucleophilic addition reactions preparation of 1,3 – oxazepine 4,7 – dione ( 8-13 ) were carried out by cyclization of appropriate Schiff bases with malic anhydride and phthalic anhydride , preparation of compounds ( 14 – 17) from reaction of a mixture aminopyridine derivative with potassium hydroxide then chloroacetic acid was added , preparation of compounds ( 18 – 20 ) from reaction of amino pyridine derivative and 4- phenyl phenacyl bromide , all these compounds were characterized by melting points and FT.IR spectroscopy. Some of them were characterized by H1- NMR and C13-NMR spectroscopy .Some compounds contain Schiff base group in compounds ( 1-7) showed inhibitory effect Candida albicans and Candida krusei .This study demonstrates that the three Candida species were resistant to a range of compounds (8-13) containing oxazepine and as antifungal against , while the compound(14-17) contain Indolin show low inhabition zon for Candida albicans and the compound (18-20) contain imidazo group showed inhibited effect against three Candida species.

Effective methodology that activates selectively either end of a carbon–carbon triple bond requires key challenge of differentiating between the multitude of C C bonds present in complex organic molecule. The synthetic strategy exploited the electronic biases within the substrate and successfully achieved site–selective [bmIm]OH catalyzed C C bond functionalization under mild reaction conditions. This resulted in C-2-selective addition of phenacyl bromide on p-substituted phenyl acetylene and C-1 selective addition on the o-substituted phenyl acetylene leading to C C bond formation. The reaction proceeded smoothly with excellent yield under ambient conditions. This report demonstrates the progress on the catalytic activity of recyclable [bmIm]OH for selective C C bond formation.

A series of novel 6-functionalized-5-amino-3-methyl-1-phenyl-1H-furo[3,2-e]pyrazolo[3,4-b]pyrazines (4a–c) was synthesized by the reaction of 3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]pyrazine-5-carbonitrile (2) with α-halocarbonyl compounds such as: diethyl 2-bromomalonate, phenacyl bromide and chloroacetone. Cyclocondensation of the amino benzoyl 4b with diethyl malonate yielded the oxopyridine carboxylate derivative 5. Also, the starting intermediate amino ester compound 4a was allowed to react with ethanol amine to afford the hydroxyethyl caboxamide derivative 6. Furthermore, hydrazinolysis of the amino ester 4a afforded the corresponding amino carbohydrazide 7 which was used as a versatile precursor for synthesis of other heterocyclic compounds attached or fused to the furopyrazolopyrazine moiety. The chemical structures of the newly synthesized compounds were confirmed on the basis of elemental and spectral analyses containing FT-IR, 1H NMR, 13C NMR, and mass spectrometry hoping ...

Two new series of bis-thiazoles 6a-f and bis-thiazolones 9a-d were prepared via reacting bis-thiosemicarbazone 3 with hydrazonoyl chloride derivatives 4a-f and 7a-d, respectively, in dioxane under basic conditions. Another group of bis-thiazole derivatives 12a-h was prepared by reacting bis-thiosemicarbazone 3 with each of phenacyl bromide derivatives 10a-h under a similar reaction protocol. A plausible mechanism was proposed. Structural elucidation of the new products was established using both elemental and spectrometric/spectroscopic analyses. Structural, electronic, and the pharmacological characteristics of the prepared molecules were investigated with DFT calculations. Antibacterial and antifungal activities of the new bis-thiazoles were screened and compared with vancomycin and amphotericin B as antimicrobial standards. Molecular docking studies on the promising candidate compounds, with the lowest minimum inhibitory concentrations (MIC), were performed with SAP2 of C. albicans and FabI of S. aureus and P. aeruginosa.

New attempts and insights are reported on the electrochemical potentiostatic reduction of phenacyl bromides in DMF. Now we present the evidences on the original mechanism proposal, the definitive characterization of the obtained products and additional results of complementary electrochemical anodic reactions.

A new series of 5-arylazo-3-cyano-2-pyridone scaffolds 5, 6 and 7 have been synthesized and characterized by elemental analysis, IR and 1H NMR spectroscopic tools. The antibacterial activities of the synthesized pyridone scaffolds have been investigated; they exhibited good activities compared to the standard drugs.

A new series of benzochromeno[2,3-d]thiazolopyrimidine derivatives were synthesized by involving 7-phenyl-10-thioxo-7,9,10,11-tetrahydro-8H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-ones with phenacyl bromide in the presence of p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions which furnished good yields. All these synthesized compounds (7a–k) were screened for their in vitro antibacterial activity against two gram positive bacteria such as (Staphylococcus aureus, Staphylococcus pyogenes) and two gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and also evaluated for their antifungal activity against four pathogenic fungal strains. All these compounds displayed good antibacterial and antifungal activity compared to reference drugs such as ciprofloxacin and mycostatin. Predominantly 7f, 7e and 7b compounds showed the highest antibacterial and antifungal activities. Moreover, all the synthesized compounds were docked against topoisomerase II DNA gyrase enzyme, which is a crucial drug target in bacteria. Docking results showed that π–π stacking and π-cationic interactions were responsible for binding interactions with the target protein.

Aim. Optimization of reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles. Materials and methods of research. The methods of organic synthesis, instrumental methods of organic compound analysis were used. Results. A scheme for the synthesis of 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles by the interaction of 5-amino-4-arylsulfonyl-3-methylthiopyrazoles 1a-b with chloroacetone, phenacyl bromide and 2-chlorocyclohexanone was developed. In contrast to the previously described interaction of substituted 5-aminopyrazoles with chloro (N-aryl) acetamides proceeding exclusively with the release of N 1 -alkylation products, in this reaction a mixture of N 1 - and N 2 -isomeric alkylation products is formed. The ratio of isomers depends on the nature of the reagents and, according to the 1H NMR-spectroscopy, is about 60:40 %.The developed technique allows with one of the synthetic procedure to carry out N 1 -alkylation of 5-aminopyrazoles 1a-b and the cyclization of products 2 in imidazo[1,2-b]pyrazoles 4a-c without isolating the N 2 -alkylation product. The purity of the obtained compounds is proved chromatographically, the structure is confirmed by the data of 1H NMR-spectroscopy. Conclusions. Optimized reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles for targeted synthesis of the novel agents for the pharmaceutical practice

The multicomponent reaction between isatin, amino acid, but-2-ynedioates, and phenacyl bromide has been developed using microwave irradiation under catalyst and base-free conditions in aqueous medium. This synthetic protocol is useful for the synthesis of various functionalized spirooxindole derivatives. This MCR exhibits a broad substrate scope with excellent yields and shorter reaction time. Additionally the synthesized spirooxindole derivatives were evaluated for their anticancer activity against three human cancer cell lines: MCF-7 (breast), A549 (lung), and HeLa cervical. Most of the compounds showed moderate to potent cytotoxic activity against the tested cell lines.

1-(3-Chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde was used in preparation of (E)-1-{[1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazol-4-yl]methylene}thiosemicarbazide. Its following reaction with ethyl bromoacetate, diethyl 2-bromomalonate, phenacyl bromide, and maleic anhydride gave pyrazolyl pharmacophore linked thiazole, thiazoline and thiazolidinone-5-carboxylic acid derivatives.

In the present manuscript, a series of steroidal thiazole derivatives (4–6, 8) have been synthesized in efficient manner by one step reaction methodology employing microwave irradiation. The synthesis involves the reaction of steroidal ketones (1–3, 7) with thiosemicarbazide and phenacyl bromide. Structural assignment of the products was confirmed on the basis of IR, 1H NMR, 13C NMR, MS and analytical data. The synthesized compounds were screened for in vitro antioxidant activity by using 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. In addition, the products 4–6, 8 were also tested for pBR322 DNA cleavage activity, genotoxicity, reactive oxygen species (ROS) production and RBC hemolysis. Molecular docking analysis was carried out to validate the specific binding mode of the newly synthesized compounds into the active site of DNA. Docking showed formation of more stable complexes of compounds 4 and 8 with the free binding energies − 8.1 and − 8 kcal/mol, respectively. Hence, it could be suggested that the steroidal compounds bearing a core thiazole scaffold would be a potent biological agent.

This Article deals with the stepwise synthesis and spectroscopic characterization of some new azo benzofuran derivatives, started from the diazotization of substituted aniline coupled with 2-hydroxy benzaldehyde. On reacting of the azo of 2-hydroxy benzaldehyde with p-bromo phenacyl bromide, the benzofuran (3a-g) are obtained. The structure of the new benzofuran derivatives have been characterized by using FT-IR, 1H-NMR,13C-NMR and DEPT-135 NMR. The biological activity of some new synthesized compound was obtained by vitro anti oxidant and anti microbial activity with both Staphylococcus aureus and Escherichia coli .The results showed that the new benzofurans have mild anti oxidant activity compared to the standard ascorbic acid.

Thirty benzofuran-2-yl(phenyl)methanones 1–30 were synthesized and characterized their structures by spectroscopic techniques. Substituted phenacyl bromide and different derivatives of 2-hydroxy-benzaldehyde treated in the presence of anhydrous K2CO3 in acetonitrile at room temperature to afford the desired benzofurans 1–30. All compounds were screened for their in vitro α-amylase inhibitory and radical scavenging (DPPH and ABTS) activities. Results revealed that para substituted compounds were found to be more active than the others with IC50 values ranges for α-amylase inhibition (IC50 = 18.04–48.33 µM), DPPH (IC50 = 16.04–32.33 µM) and ABTS (IC50 = 16.99–33.01 µM) radical scavenging activities. Activities results were compared with the standards acarbose (IC50 = 16.08 ± 0.07 µM) for α-amylase, ascorbic acid (IC50 = 15.08 ± 0.03 and 15.09 ± 0.17 µM) for DPPH and ABTS radical scavenging activities, respectively. Kinetic studies predicted that all compounds followed non-competitive mechanism of inhibition. Molecular docking results showed good protein–ligand interactions profile against the corresponding target. To the best of our knowledge, out of thirty molecules, ten compounds 18–20, 22, and 25–30 were structurally new.

Background: In chemistry, the derivatives of benzofuran which are substituted on five-membered ring constitute one of the salient moieties in medicinal field and a survey of literature revealed that a good number of reports have shown that tetrahydrobenzofuran derivatives are of valuable biological activities. Aim: On the basis of previous survey, we aimed to generate a series of 2-(4-azidobenzoyl)-3-substitutedaryl-6,6-dimethyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one bearing azide group which were identified by anti-cancer screening against sixteen cell-lines of NCI (National Cancer Institute) using nine different cancer cell panels. Materials and methods: The tetrahydrobenzofuran derivatives were synthesized by multi-component reactions. It was achieved by coupling of dimedone (3.57 mmole), 4-azido phenacyl bromide (3.92 mmole) and various aromatic aldehydes (3.57 mmole) using two different bases i.e. pyridine and N,N- diethylethanamine under reflux condition. Anti-cancer activity was carried out by NCI-60 cell-lines using standard protocol by National Institute of Health. Results: The results from anti-cancer study shows that the compound 4a exhibited diverse cytotoxic activity against renal cancer panel (UO-31) with significant selectivity and had inhibitory effect on the generation of UO-31 (growth percent= 69.36%) and the compound 4e showed comparable activity in the same cell-line (UO-31: growth percent= 80.86%). Conclusions: In summary, a series of azide group containing tetrahydrobenzofuran derivatives have been synthesized and were evaluated for their anticancer activity. It was concluded that the derivatives 4a and 4e exhibited promising anticancer activity. Nature of substituent on phenyl ring seems to be the crucial factor affecting the activity in both the compounds.

An efficient diastereoselective synthesis of spirocyclopropaneoxindoles is reported using three-component reactions of various phenacylidenetriphenylphosphorane, isatins and phenacyl bromide under ultrasonic irradiation. The structures of synthesized spirocyclopropaneoxindoles were characterized by their spectral data. The antioxidant activities of the synthesized compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Among the products, those with NH group in their structure exhibited higher antioxidant activities than other derivatives. Also, in vitro cytotoxicity of compounds 4b, 4e, 4j, 4k were examined against heLa cancer cell lines using MTT assay. The results revealed that compound 4j with chlorine substituent on phenyl group displayed higher cytotoxicity activity (IC50 =4.50±0.30 μg/mL) after 48 h.

The chemical structure of pyrazole-1-carbothioamide derivative 1 was modified through building a thiazole moiety to synthesize derivatives of thiazolyl pyrazolin-5-one. The reaction of 1 with phenacyl bromide furnished the conforming thiazolyl pyrazole derivative 2, which upon base-catalyzed reaction with benzyl isothiocyanate afforded thiazolyl 4-(benzylthiocarbamoyl)-2-pyrazolin-5-one derivative 3. The diazo-coupling reaction of 2 with diazotized 4-aminoacetophenone afforded the conforming thiazolyl 4-(p-acetylphenylhydrazono)-2-pyrazolin-5-one derivative 4. The synthesized thiazolyl pyrazolin-5-one derivatives were utilized as antioxidant additives for lubricating oil. The oxidation stability study revealed that the tested compounds showed good antioxidant activities. The efficiency of the tested antioxidant additives decreases according to the order: compound 2 > compound 4 > compound 3 > compound 1.

A cryogenic ion trap vibrational spectrometer is combined with a microfluidic chip reactor in a proof-of-principle experiment on the Hantzsch cyclization reaction forming 2-amino-4-phenyl thiazole from phenacyl bromide and thiourea. First, the composition of the reaction solution is characterized using electrospray-ionization mass spectrometry combined with two-color infrared photodissociation (IRPD) spectroscopy. The latter yields isomer-specific vibrational spectra of the reaction intermediates and products. A comparison to results from electronic structure calculations then allows for an unambiguous structural assignment and molecular-level insights into the reaction mechanism. Subsequently, we demonstrate that isomeric and isobaric ions can be selectively monitored online with low process time, i.e., using a single IRPD wavelength per isomer, as the chip reaction parameters are varied.

A novel and atom-economic protocol for the synthesis of thiazole-2-imine derivatives was developed. Synthesis of thiazole-2-imine derivatives from primary amines, phenyl isothiocyanate and phenacyl bromide derivatives by the CoFe2O4@SiO2-PA-CC-Guanidine-SA magnetic nanocatalyst in excellent yields was reported. This nanocatalyst is easily separated from the reaction mixture and can be reused for several times. For the characterization of the catalyst used of Fourier-transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), thermogravimetric analysis (TGA) and vibrating-sample magnetometry (VSM) techniques.

Ten new pyridine linked various substituted thiazole hybrids through (hydrazonomethyl)phenoxy-acetamide spacer were synthesized. The synthetic strategy was based on the reaction of the precursor 2-(4-((2-carbamothioylhydrazono)methyl)phenoxy)-N-(pyridin-2-yl)acetamide (3) with various α-halogenated carbonyl compounds (namely; phenacyl bromides, ethyl bromoacetate, diethyl bromomalonate and 3-chloropentane-2,4-dione). Moreover, the cytotoxicity properties of the synthesized compounds have been studied against liver carcinoma (HepG2), laryngeal carcinoma (Hep-2), prostate cancer (PC3), breast cancer (MCF-7) and normal fibroblast cells (WI38). The pyridine-thiazole compounds 7 and 10 revealed promising anticancer activity against MCF-7 and HepG2 cell lines with IC50 values in the range 5.36–8.76 μM compared to the activity of 5-fluorouracil. Docking study provided valuable insights for binding sites of the synthesized compounds with Rho-associated protein kinase (ROCK-1).

Bio-active steroidal imidazoles 7–9 were synthesised by reacting steroidal thiosemicarbazones 4–6 with phenacyl bromide. After characterisation by spectral and analytical data, the interaction of compounds 7–9 with DNA were carried out by UV-vis, luminescence spectroscopy and gel electrophoresis. The compounds bind with DNA preferentially through electrostatic and hydrophobic interactions with K b; 3.14 × 104, 6.27 × 104 and 5.17 × 104 M−1, respectively indicating higher binding affinity of compound 8 towards DNA. Gel electrophoresis depicted the concentration dependent cleavage activity of compound 8 with supercoiled pBR322. The docking study revealed the minor groove binding of compounds with DNA and intercalation between the nucleotide base pairs is due to imidazole moiety. In Dimethyl thiazolyl diphenyl tetrazolium bromide assay, compounds 7 and 8 showed promising activity against different human cancer cells especially against A545, HepG2 and MCF7 cells. The uptake of compounds by HepG2, MCF7 and A549 cells was studied by confocal microscopy. The Genotoxic nature of compounds 7 and 8 was studied by the comet assay while as the relative expressions of apoptotic markers of A545 cells after interacting with steroidal imidazoles was studied by western blotting analysis.

Thiazoles and their derivatives have attracted continuing interest in both pharmaceutical and agrochemical industries and shows significant importance for the discovery of potent bioactive agents due to their various biological activities. The present study reports the synthesis of novel 2-{2-[(6-methoxynaphthalen-2-yl) methylidene] hydrazinyl}4-(aryl)-1, 3-thiazole (5a-5j) which was synthesized by acid hydrolysis of 6-methoxynaphthalene-2carbaldehyde (1) and hydrazinecarbothioamide (2) which was refluxed for around 10 hours using alcohol as solvent, to yield (2E)-2-[(6-methoxynaphthalen-2-yl) methylidene] hydrazinecarbothioamide (Thiosemicarbozone) (3). The compound (3) was then condensed with different substituted phenacyl bromide (4) at 90 o C for 8-9 hours .The structures of newly synthesized compounds were characterized by IR, 1 H-NMR, 13 C -NMR and mass spectroscopic studies, few of the synthesized compounds showed moderate anti-TB activities and compounds (5d) showed moderate activity against M.tuberculosis (H37 RV Strain).Among the compounds screened for antibacterial activity (5c), (5e), (5g) and (5h) showed excellent antibacterial activity.