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The impact of successive replacement of K+ by Na+ on the megahertz–gigahertz polarization response of 0.25[fKSCN + (1 − f)NaSCN] + 0.75CH3CONH2 deep eutectic solvents (DESs) was explored via temperature-dependent (303 ≤ T/K ≤ 343) dielectric relaxation (DR) measurements and computer simulations. Both the DR measurements (0.2 ≤ ν/GHz ≤ 50) and the simulations revealed multi-Debye relaxations accompanied by a decrease in the solution static dielectric constant (ɛs) upon the replacement of K+ by Na+. Accurate measurements of the DR response of DESs below 100 MHz were limited by the well-known one-over-frequency divergence for conducting solutions. This problem was tackled in simulations by removing the zero frequency contributions arising from the ion current to the total simulated DR response. The temperature-dependent measurements revealed a much stronger viscosity decoupling of DR times for Na+-containing DES than for the corresponding K+ system. The differential scanning calorimetry measurements indicated a higher glass transition temperature for Na+-DES (∼220 K) than K+-DES (∼200 K), implying more fragility and cooperativity for the former (Na+-DES) than the latter. The computer simulations revealed a gradual decrease in the average number of H bonds (⟨nHB⟩) per acetamide molecule and increased frustrations in the average orientational order upon the replacement of K+ by Na+. Both the measured and simulated ɛs values were found to decrease linearly with ⟨nHB⟩. Decompositions of the simulated DR spectra revealed that the cation-dependent cross interaction (dipole-ion) term contributes negligibly to ɛs and appears in the terahertz regime. Finally, the simulated collective single-particle reorientational relaxations and the structural H-bond fluctuation dynamics revealed the microscopic origin of the cation identity dependence shown by the measured DR relaxation times. [ABSTRACT FROM AUTHOR]

A series of 2-benzimidazolamine-acetamide derivatives were synthesized by substitution reaction of different anilines with chloroacetyl chloride followed by the reaction of 2-aminobenzimidazole with the formed substituted chloroacetamides. The structures of all the synthesized compounds were elucidated with various spectral techniques and all compounds were evaluated against five bacterial strains. Out of ten, the N -(2-fluorophenyl)-substituted acetamide displayed better minimum inhibitory concentration (MIC). Disk diffusion assay and combination studies were also performed on the same acetamide compound. Molecular docking of this acetamide compound with E. coli methionine aminopeptidase (METAP) displayed effective binding, and molecular dynamics simulation further suggested a stable complex formation. Thus, all these results indicate that these scaffolds can serve as a model for developing antibacterial agents. [ABSTRACT FROM AUTHOR]

An unprecedented post-Ugi Brønsted acid catalyzed fragmentation followed by in situ trapping of the alkylideneindolenine intermediate by indole nucleophiles was developed to furnish novel bis(indolyl)acetamides. The amide fragment formed during this acid-catalyzed fragmentation of the Ugi adduct was also isolated and characterized. The carboxylic acid and amine components of the Ugi reaction were carefully chosen to permit a simple water wash for the removal of the amide fragment to obtain the desired bis(indolyl)acetamides in a pure form. [ABSTRACT FROM AUTHOR]

The oxalamide skeleton is a common structural motif in many biologically active molecules. These scaffolds can be synthesized via ruthenium pincer complex-catalyzed acceptorless dehydrogenative coupling of ethylene glycol and amines. In this study, we elucidate the mechanism of this oxalamide synthesis using density functional theory calculations. The rate-determining state is identified as the formation of molecular hydrogen following the oxidation of hydroxyacetamide to oxoacetamide. In predictive catalysis exercises, various modifications to the ruthenium pincer catalyst were investigated to assess their impact on the reactivity. [ABSTRACT FROM AUTHOR]

Two novel mononuclear palladium(II) complexes, [PdL1Cl]Cl (1) and [PdL2Cl]Cl (2) with SNS-donor ligands [where L1 = N-(4-(benzo[d]oxazol-2-yl)phenyl)-2-(bis(2-ethylthioethyl)amino)acetamide, L2 = N-(4-(benzo[d]thiazol-2-yl)phenyl)-2-(bis(2-ethylthioethyl)amino)acetamide], were synthesized and characterized. In vitro antiproliferative activity tests showed that the two palladium(II) complexes displayed excellent antiproliferative activity against all tested cancer cell lines, especially human colon cancer HCT-116, human liver cancer HepG-2, and human breast cancer MDA-MB-231 cells. Spectacularly, complexes 1 and 2 exhibited approximately 8.49- and 6.88-fold higher antiproliferative activity, as compared with cisplatin, against HCT-116, respectively, but were less toxic to human normal colon fibroblast CCD-18Co cell lines with selectivity index (SI = IC50(CCD-18Co)/IC50(HCT-116)) values of 22.43 and 21.48 for 1 and 2, respectively, compared to that of cisplatin (SI, 1.74). These results suggested that the two palladium complexes have the potential to act as candidates for the treatment of colorectal cancer. The interaction of the complexes with CT-DNA and pUC19 plasmid DNA illustrated that both 1 and 2 could strongly bind to the DNA helix via an intercalative mode and covalent interaction and perturb the tertiary structure of DNA, where the DNA binding affinity of 1 was slightly higher than that of 2. Additionally, investigations of the reaction of the two complexes with 5′-GMP and glutathione (GSH) showed that both 1 and 2 could readily react with 5′-GMP and GSH to form Pd-GMP adducts and Pd-GS adducts, respectively, and when 5′-GMP and GSH coexisted, the coordination binding of the complexes with GSH did not prevent the formation of the Pd-GMP adducts. Moreover, Hoechst 33342 staining and flow cytometry analysis demonstrated that the two palladium(II) complexes arrested HCT-116 cells mainly at the G2/M phase, induced mitochondrial-membrane depolarization, increased ROS generation, and triggered obvious cell apoptosis. [ABSTRACT FROM AUTHOR]

A new indole compound, N-hydroxy-N-(2-(1-hydroxy-2-methoxy-1H-indol-3-yl)ethyl acetamide (1), together with four known compounds, N-(2-(1H-indol-3-yl)ethylacetamide (2), N-acetylamicoumacin C (3), N-(2-phenylethyl)acetamide (4), and (2 R,3S)-1-(4-hydroxyphenyl)butane-2,3-diol (5) were isolated from Cladosporium sp. SCSIO41205. Their structures were established by detailed analysis of the NMR and HR-ESI-MS data. [ABSTRACT FROM AUTHOR]

In the title molecule, C13H17N3O3, the substituents on the phenyl ring are rotated slightly out of the mean plane of the ring but the piperidine moiety is nearly perpendicular to that plane. In the crystal, C--H···O hydrogen bonds form chains of molecules extending along the c-axis direction, which are linked by C O···π(ring) interactions. A Hirshfeld surface analysis showed the majority of intermolecular interactions to be H···H contacts while O···H/H···O contacts are the second most numerous. [ABSTRACT FROM AUTHOR]

The "New Journal of Chemistry" published by The Royal Society of Chemistry features a variety of research papers on topics such as catalysis, materials science, and environmental chemistry. The latest issue includes papers on topics like the synthesis of nanomaterials, electrocatalysis, and the development of new catalysts for chemical reactions. The journal aims to connect the global chemistry community and reinvest profits back into the field. [Extracted from the article]

Three new tertiary phosphane-appended heteroleptic Ni(II)-dithiolates with the formula [Ni(CAM)(dppe)] (Ni-1), [Ni(CAM)(dppf)] (Ni-2) and [Ni(CAM)(PPh3)2] (Ni-3) (CAM = cyanoacetamide dithiolate; dppe = 1,2-bis-(diphenylphosphinoethane); dppf = 1,1′-bis-(diphenylphosphino)ferrocene and PPh3 = triphenylphosphane) have been synthesized and characterized spectroscopically and using single crystal X-ray diffraction technique. The single crystal X-ray analysis of Ni-1, Ni-2 and Ni-3 reveal distorted square planar geometry around Ni(II), wherein Ni(II) is coordinated to the two sulfur centres of a CAM ligand in the bidentate chelating mode and two phosphorus centers of dppe, dppf and PPh3 ligands. Solid-state frameworks in these complexes are stabilized by C–O⋯H, C–N⋯H, C–S⋯H and C–H⋯C non-covalent intermolecular interactions. Ni-2 exhibits intramolecular (Ar)C–H⋯Ni anagostic interaction, which is absent in Ni-1 and Ni-3. Ni-3 exhibits intramolecular π⋯π stacking between the phenyl rings. The nature of these interactions have been assessed using Hirshfeld surface analyses, density functional theory (DFT) and quantum theory of atoms-in-molecules (QTAIM) calculations. Furthermore, the complexes have been employed as a homogeneous electrocatalyst for electrochemical hydrogen evolution reactions (HERs) using trifluoroacetic acid (TFA) as the hydrogen source. Electrochemical studies reveal turnover frequency (TOF) values of 319, 341 and 543 s−1 for Ni-1, Ni-2 and Ni-3, respectively, at 50 mM concentration of TFA. The plausible reason for the relatively better electrocatalytic activity of Ni-3 is ascribed to the coordination flexibility of the PPh3 ligand and the relatively larger positive natural charge over the nickel center and smaller HOMO–LUMO energy gap. [ABSTRACT FROM AUTHOR]

Sulfonamide derivatives as semiconductor materials for organic optoelectronic devices, including photovoltaic (PV), have received considerable interest. In the present work, the synthesis of novel pyrogallol-sulfonamide derivatives based on a molecular hybridization approach yielded N-((4-((2,3,4-trihydroxyphenyl)diazenyl)phenyl)sulfonyl)acetamide (N-DPSA). The techniques of spectroscopy, Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (1H NMR), and mass spectrum were utilized to identify the structural composition of the synthesized N-DPSA. The new N-DPSA was investigated by Hall-effect measurement to prove the positive charge carrier (hole mobility) with mobility and conductivity of 2.39 × 103 cm2/Vs and 1.76 × 10–1 1/Ω cm, respectively. Consequently, N-DPSA could be proposed as a strong candidate as a p-type semiconductor (hole transport layer (HTL)). The optical energy gap was computed at 2.03 eV, indicating the direct optical transition nature of N-DPSA. The elaborated molecular semiconductor's thermal features, molecular modelling, and electronic energy levels were also investigated. The new N-DPSA at various concentrations provided easy synthesis, cheap cost, high performance, and a straightforward design approach for a possible HTL in effective perovskite solar cells (PSCs). A PCE of 7.3% is shown for the N-DPSA-based PSC at its optimal concentration. [ABSTRACT FROM AUTHOR]

In the title molecule, C20H18ClN3O2, the 2-chlorophenyl group is disordered to a small extent [occupancies 0.875 (2)/0.125 (2)]. The phenylacetamide moiety is nearly planar due to a weak, intramolecular C—H...O hydrogen bond. In the crystal, N—H...O hydrogen bonds and π-stacking interactions between pyridazine and phenyl rings form helical chains of molecules in the b-axis direction, which are linked by C—H...O hydrogen bonds and C—H...π(ring) interactions. A Hirshfeld surface analysis was performed, which showed that H...H, C...H/H...C and O...H/H...O interactions to dominate the intermolecular contacts in the crystal.

The compounds 2-chloro-N-(3-methoxyphenyl)acetamide (m-acetamide) and 2-(3-methoxyphenylamino)-2-oxoethyl methacrylate (3MPAEMA) were synthesized in this study for the first time in the literature. FTIR, 1H, and 13C NMR spectroscopic techniques were used to characterize it. Subsequently, computational techniques were used to assess various ADME factors, such as drug-likeness properties, bioavailability score, and adherence to Lipinski's rule. Finally, molecular docking experiments were conducted with the human topoisomerase α2 (TOP2A) protein to verify and validate the reliability and stability of the docking procedure. The results of the docking scores, which quantify binding affinity, indicated that these derivatives exhibited a stronger affinity for TOP2A. [ABSTRACT FROM AUTHOR]

N-(5-((3E,5E)-10-Acetoxy-5,7,9,11-tetramethyltrideca-3,5-dien-1-yl)-2-oxotetrahydrofuran-3-yl)acetamide (1), a new amide compound, and five known ones (2–6) were isolated from the EtOH extract of the solid culture of Fusarium sp. Their structures were determined by means of extensive 1D and 2D NMR techniques, as well as comparison with literature values. Additionally, compounds 1–6 were tested for their cytotoxic activities. The results showed that compounds 2, 3, 6 exhibited cytotoxic activities against five human cancer cell lines with IC50 values ranging from 2.088 to 26.40 μM. [ABSTRACT FROM AUTHOR]

Novel 2-imino-6-(aryldiazenyl)-2H-chromene-3-carboxamides 6a–e, 2-amino-4H-cyclopenta or benzo[b]thiophene-3-carboxamides 10a,b, 2,7-diaminopyrazolo[1,5-a]pyrimidine-6-carboxamides 13a–e, pyrimidine-5-carboxamides 14, 15 and 3-amino-1H-pyrazole-4-carboxamide 16 were synthesized from the reaction of 2-cyano-N-(1,3-dihydroxy-2-(hydroxyl-methyl) propan-2-yl) acetamide 2 with 4-arylazosalicylaldehydes 5a-e, cyclopentanone and/or cyclohexanone, guanidine derivatives and hydrazine hydrate, respectively. Some new compounds were evaluated for antibacterial activity in vitro, and exhibited good efficacy compared to gentamicin. Compound 4c showed greater activity against gram negative bacteria (Klebsiella pneumonia and Pseudomonas aeruginosa) than standard antibiotic. Compound 4c with two withdrawing groups also showed the higher activity (38.7 ± 0.6) against fungi (Candida albicans) than the Nystatin (20 ± 0.5). On the other hand, compounds 13a, 13c, and 13e have strong cytotoxic activity among the tested compounds in the three selected cancer cell lines (HePG2, MCF7 and Hela). Physicochemical characterization by Swiss ADME predication was also performed for some synthesized compounds exhibiting better biological and antimicrobial properties. [ABSTRACT FROM AUTHOR]

In the title mol­ecule, C20H18ClN3O2, the 2-chloro­phenyl group is disordered to a small extent [occupancies 0.875 (2)/0.125 (2)]. The phenyl­acetamide moiety is nearly planar due to a weak, intra­molecular C—H⋯O hydrogen bond. In the crystal, N—H⋯O hydrogen bonds and π-stacking inter­actions between pyridazine and phenyl rings form helical chains of mol­ecules in the b-axis direction, which are linked by C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions. A Hirshfeld surface analysis was performed, which showed that H⋯H, C⋯H/H⋯C and O⋯H/H⋯O inter­actions to dominate the inter­molecular contacts in the crystal. [ABSTRACT FROM AUTHOR]

This study focuses on the systematic exploration of the emodepside conformations bound to monovalent K+ ion using quantum mechanical density functional theory (DFT) calculations at the M06‐2X/6‐31+G(d,p) level of theory. Nine conformers of emodepside and their complexes with K+ ion were characterized as stationary points on the potential energy surface. The conformational isomers were examined for their 3D structures, bonding, energetics, and interactions with the cation. A cavitand‐like structure (CC) is identified to be the energetically most stable arrangement. To arrive at a better understanding of the K+ ion binding, calculations were initially performed on complexes formed by the K+ and Na+ ions with model ligands (methyl ester and N,N‐dimethyl acetamide). Both the natural bond orbital (NBO) method and the block‐localized wavefunction (BLW) energy decomposition approach was employed to assess the bonding and energetic contributions stabilizing the ion‐bound model complexes. Finally, the solvent effect was evaluated through complete geometry optimizations and energy minimizations for the model ion‐ligand complexes and the emodepside‐K+ bound complexes using an implicit solvent model mimicking water and DMSO. [ABSTRACT FROM AUTHOR]

Nine new coumarin derivatives of 2‐(7‐hydroxy‐2‐oxo‐2H‐chromen‐4‐yl)acetic acid 6a–i have been successfully synthesized through amide coupling with various substituted anilines and 2‐aminopyridines. The synthesized derivatives were screened for anticancer activity using MTT assay on MCF‐7 cell line. The results showed that compound 6b inhibited MCF‐7 cell growth in a dose‐dependent manner and reached 47% inhibition at 40 µM, being better than starting material 5 and references 3 and 5FU drug. Moreover, 6b inhibited significantly 3D tumorsphere formation. The para‐Br substitution of 6b seems to be important for activity. Docking study suggests estrogen receptor and/or 3a‐HSD type 3 protein could be the target(s) for anticancer activity of this class of compounds. Further optimization of compound 6b should lead to more potent compound. [ABSTRACT FROM AUTHOR]

Azo coupling reactions of (Z)-2-(3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)ylidene)-N-(2,4-xylyl)-acetamide with diazonium salts were used to synthesize 2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-2-(2-arylhydrazono)-N-(2,4-xylyl)-acetamides. All compounds showed analgesic effects in the hotplate test, exceeding the effect of metamizole sodium. In the case of the most active hydrazone, the defensive reflex time in mice was 27.10 min (compared with 16.60 min for metamizole sodium). [ABSTRACT FROM AUTHOR]

Offering ultrahigh energy density and exceptional safety, all‐solid‐state lithium–sulfur batteries (ASSLSBs) can be one of the most promising energy storage systems if their inherent challenges, including slow Li+ mass transport and insufficient sulfur utilization efficiency, are completely tackled. In this work, an amide‐based electrolyte additive with a high Gutmann donor number is used to construct a deep eutectic system, a “one‐stone‐two‐birds” solution to address these issues. In particular, an acetamide is used to interact with the insulative Li2S via a strong S─H bond and Li─O bond to boost the electrochemical reaction kinetics of lithium‐sulfur (Li─S) chemistry and sulfur utilization and simultaneously form a deep eutectic LiTFSI‐acetamide system to enhance ionic conductivity of solid polymer electrolytes (SPEs). Such a seamless integration of this system into the solid‐state LSBs helps deliver a high initial discharge specific capacity of 1012 mAh g−1 at 0.05 C and attain a stable cyclability for 1300 cycles at 0.1 C. This remarkable achievement in high performance and stability can effectively facilitate the commercialization of ASSLSBs. [ABSTRACT FROM AUTHOR]

A range of fused heterocyclic compounds are generated utilizing the crucial intermediary 2-cyano-N-(2,5-dioxopyrrolidin-1-yl) acetamide 4. Spectral analysis was executed to support the structures of the newly synthesized compounds, which is expected to have a potential biological activity. The antimicrobial activity of the recently synthesized compounds and their derivatives has been tested against B. subtilis, S. aureus, E. coli, P. aeruginosa, S. typhimurium, C. albicans, and A. niger, as reference antibiotics, ampicillin and mycostatin, were used against test bacteria and fungi, respectively. In general, the novel produced compounds demonstrated a good antibacterial action against the previously indicated pathogens. [ABSTRACT FROM AUTHOR]

A highly effective approach has been proposed for the synthesis of unique imidazole aniline compounds via a reaction sequence including acylation of substituted anilines with 2-chloroacetyl chloride, alkylation of 2-butyl-5-chloro-1H-imidazole-4-carbaldehyde with the resulting 2-chloroacetanilides, and con-densa-tion of 2-(2-butyl-5-chloro-4-formyl-1H-imidazol-1-yl)-N-(substituted phenyl)acetamides with 4-{4-[5-(amino-methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. The newly synthesized compounds have been screened for their in vitro antimalarial potential against Plasmodium falciparum and found to exhibit incredibly impressive half-maximum inhibitory concentration (IC50) values. Molecular docking has been performed for the most active compound and dihydrofolate reductase–thymidylate synthase (DHFR-TS) from the wild-type Plasmodium falciparum, and hydrogen bond interactions between the amino acid residues Ser167 and Ser111 and azomethine and imidazole nitrogen atoms, respectively, have been revealed. [ABSTRACT FROM AUTHOR]

The novel Schiff bases 3a-d were synthesized by reacting 6-methyl--2-aminobenzothiazole and different substituted benzaldehydes. Afterwards, the obtained Schiff bases were reduced with NaBH4 to form amine compounds 4a-d. In the final step, reaction of the amine with chloroacetyl chloride gave the novel amide derivatives 5a-d. The structures of the all novel synthesized compounds were characterized by FT-IR, ¹H-NMR, 13C-NMR, ESI MS, HETCOR, 2D (¹H-¹H) COSY spectra and elemental analyses. The antimicrobial activities of the novel synthesized compounds, were tested against some Gram-positive and Gram-negative bacterial as well as fungal species and the results were discussed. [ABSTRACT FROM AUTHOR]

Sn-Pb perovskite solar cells, which have the advantages of low toxicity and a simple preparation process, have witnessed rapid development in recent years, with the power conversion efficiency for single-junction solar cells exceeding 23%. Nevertheless, the problems of poor crystalline quality of Sn-Pb perovskite films arising from rapid crystallization rate and facile oxidation of Sn2+ to Sn4+ have become key issues for the further development of Sn-Pb perovskite solar cells. Herein, we report the incorporation of triazinamide (N-(6-methyl-3-oxo-2,5-dihydro-1,2,4-Triazin-4(3H)-YL) acetamide) as an additive to regulate the crystalline growth of Sn-Pb perovskite films, resulting in films with low trap density and large grain size. The triazinamide additive effectively passivated defects in the perovskite films. As a result, the triazinamide-modified perovskite solar cells achieved a higher efficiency of 15.73%, compared with 13.32% for the control device, significantly improving device performance. Notably, the optimal triazinamide-modified perovskite solar cell maintained 72% of its initial power conversion efficiency after being stored in an air environment for nearly 300 h, while only 18% of the power conversion efficiency of the control perovskite solar cell was retained. This study proposes an effective strategy for fabricating highly efficient and stable Sn-Pb perovskite solar cells. [ABSTRACT FROM AUTHOR]

Frequency-dependent dielectric relaxation in three deep eutectic solvents (DESs), (acetamide+LiClO4/NO3/Br), was investigated in the temperature range, 329 ≤ T/K ≤ 358, via molecular dynamics simulations. Subsequently, decomposition of the real and the imaginary components of the simulated dielectric spectra was carried out to separate the rotational (dipole–dipole), translational (ion–ion), and ro-translational (dipole–ion) contributions. The dipolar contribution, as expected, was found to dominate all the frequency-dependent dielectric spectra over the entire frequency regime, while the other two components together made tiny contributions only. The translational (ion–ion) and the cross ro-translational contributions appeared in the THz regime in contrast to the viscosity-dependent dipolar relaxations that dominated the MHz–GHz frequency window. Our simulations predicted, in agreement with experiments, anion-dependent decrement of the static dielectric constant (ɛs ∼ 20 to 30) for acetamide (ɛs ∼ 66) in these ionic DESs. Simulated dipole-correlations (Kirkwood g factor) indicated significant orientational frustrations. The frustrated orientational structure was found to be associated with the anion-dependent damage of the acetamide H-bond network. Single dipole reorientation time distributions suggested slowed down acetamide rotations but did not indicate presence of any "rotationally frozen" molecule. The dielectric decrement is, therefore, largely static in origin. This provides a new insight into the ion dependence of the dielectric behavior of these ionic DESs. A good agreement between the simulated and the experimental timescales was also noticed. [ABSTRACT FROM AUTHOR]

Two new [1-(phenylsulfonyl)-1H-indol-2-yl]methanamine derivatives, namely, N-(3-methoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}acetamide, C24H22N2O4S, (I), and N-(2,5-dimethoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide, C29H26N2O6S2, (II), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C—H...O bonding [C...O = 3.312 (4)–3.788 (8) Å], with the structure of II exhibiting a larger number, but weaker bonds of this type. Slipped π–π interactions of antiparallel indole systems are specific for I, whereas the structure of II delivers two kinds of C—H...π interactions at both axial sides of the indole moiety. These findings agree with the results of Hirshfeld surface analysis. The primary contributions to the surface areas are associated with the contacts involving H atoms. Although II manifests a larger fraction of the O...H/H...O contacts (25.8 versus 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations.

Streamline synthesis of cyclic alcohols has been an enduring goal in synthetic chemistry. In this regard, a series of aminoquinoline‐based pincer ligands (L1(H)=2‐(dimethylamino)‐N‐(quinolin‐8‐yl)acetamide, L2(H)=2‐(diethylamino)‐N‐(quinoline‐8‐yl)acetamide, L3(H)=2‐(dipropylamino)‐N‐(quinoline‐8‐yl)acetamide and L4(H)=2‐(dibutylamino)‐N‐(quinolin‐8‐yl)acetamide)) and corresponding nickel(II) complexes of the type [Ni(L)Cl] (1–4) were synthesized and characterized using modern analytical techniques. Further, the catalytic activity of 1–4 was investigated for the oxidation of cyclohexane in the presence of different oxidants. All the catalysts showed substantial activity in the presence of m‐CPBA as the oxidant in DCM‐CH3CN (v/v, 3 : 1) solvent mixture at 60 ° C to yield cyclohexanol as the major product and cyclohexanone and caprolactone as the minor products. Under the optimised reaction conditions, catalytic activity was in the order 1 (936)>2 (892)>3 (835)>4 (785), which can be rationalized by the steric‐electronic properties of the respective ligands. Notably, with catalyst 1, we could achieve the highest TON (936) reported so far for cyclohexane oxidation using nickel(II) complexes having square planar geometry. The best catalyst, 1 was further used for the oxidation of other cycloalkanes and showed appreciable activity. The formation of chlorinated products in the reaction and product distribution pattern revealed that the oxidation is mediated majorly by 3‐chlorobenzoyloxy radical. [ABSTRACT FROM AUTHOR]

Deep eutectic solvents (DESs) are gaining rapid prominence in numerous biocatalysis processes due to their green characteristics, biodegradability, low cost, and simple preparation compared to harsh organic solvents and toxic ionic liquids. However, natural enzymes tend to show activity reduction, even inactivation in the presence of many DESs. Here, we present the first rational design approach to achieve enzymes resistant to both DESs and high temperatures. Using the interaction pattern between DESs and BSLA (Bacillus subtilis lipase A, our model enzyme) derived from all-atom molecular dynamics (MD) simulations, we formulated a solvation-guided engineering strategy. This was established after assessing 33 structural, solvation, and energy observables. We rationally designed and experimentally tested 36 single substitutions, of which 28 (a 77.78% success rate) exhibited improvements in at least two DES cosolvents: choline chloride (ChCl) : acetamide, tetrabutylphosphonium bromide (TBPB) : ethylene glycol (EG), and ChCl : EG. Additionally, through stepwise recombination, we identified two robust BSLA variants, D64H/R107L/E171Y and D64H/R142L, showing stability improvements of up to 4.4-fold and 3.2-fold in three DESs and at 50 °C, respectively. Further MD studies demonstrated that (i) the restricted overall structure but fine-tuned local flexibility and (ii) increased water but decreased DES molecules at substituted sites are two main factors contributing to the enhanced multiple DES resistance. Overall, solvation-guided engineering offers an efficient and rational approach for designing lipases tolerant to DES cosolvents and elevated temperatures, with a considerable potential for adaptation to other enzymes. [ABSTRACT FROM AUTHOR]

Influenza virus transmission is largely mediated by its mutation and genome reassortment from distinct strains resulting in drug-resistances and pandemics. This necessitates the need for the discovery of more potential influenza inhibitors to prevent future epidemics. An in-silico approach was utilized here to design six new (21a-f) potential inhibitors of influenza neuraminidase (NA) using a hit compound 21 with good binding affinity, pre- dicted activity, and pharmacokinetic properties in our previous work. The modeled activities (pEC50) of the newly designed compounds (ranging between 8.188 and 7.600) were better than that of the hit compound 21 with predicted activity (pEC50) of 6.0101 and zanamivir (pEC50 of 5.6755) as the standard reference control used. The MolDock scores (ranging between-189.67 and 142.47 kcal/mol) of these newly designed compounds in the NA binding cavity were also better than the hit template 21 with a MolDock score of-125.33 kcal/mol and zanamivir standard drug (-136.36 kcal/mol). In addition, the conformational stability of the best-designed compound 21a in the NA binding cavity was further studied through the MD simulation of 100 ns. Moreover, the drug-likeness and ADMET predictions of these designed compounds showed their good oral bioavailability and pharmacokinetic profiling respectively. More so, the DFT calculations also revealed the relevance of these designed com- pounds in view of their smaller band energy gaps from the frontier molecular orbital calculations. This study could serve as a reliable in-silico perspective for the search and discovery of potential anti-influenza agents. [ABSTRACT FROM AUTHOR]

The present work details the synthesis of several intriguing nitrogenous heterocycles utilizing a cyano-N-aryl-acetamide-reagent, notably chlorinated thiazolidine, thiophene and 2-iminochromene derivatives. Thus, the precursor 2-cyano-N-(2,4-dichlorophenyl) acetamide 1 underwent the reaction with phenyl isothiocyanate in DMF/KOH to afford the intermediate salt 3, which reacted in situ with several α-halogenated reagents 4a-c like ethylchloroacetate,α-bromoethylpropionate and α-bromo ethyl butaneoate and afforded the corresponding 4-thiazolidinnone derivatives (6a–c, yield%; 67–85), thiophene derivatives (11;yield 80%) and (15, yield 77%) obtained from the reaction of 3 with α- chloroacetyl acetone 9 and ethyl 2-chloro-3-oxobutanoate 12.Novel series of different 4-thiazolidinones(16a–e; yield%; 65–84) were obtained via condensation of 6a with different aldehydes. Finally, the reaction of compound 1 with different bifunctional reagents, such as salicylaldehyde derivatives and 2-hydroxynaphthaldehyde, in ethanol furnished the iminochromenes (17a,b; yield %77,80) and (18; yield 85%). In addition, molecular docking studies of the prepared molecules were carried out against papain-like protease (PLpro) to identify novel promising inhibitors of Coronavirus Disease COVID-19. The binding affinity of the best docked compounds 16c and 16a toward the target enzyme was − 9.6 and − 8.9 kcal/mole, respectively. In silico-docking-Studies indicate, that compounds 16c and 16a have the potential as antiviral against COVID-19. [ABSTRACT FROM AUTHOR]

Electrodeposited iron films demonstrate commendable attributes such as a high magnetic flux density and enhanced stability. Nevertheless, the occurrence of the hydrogen evolution side reaction during the electrodeposition of iron films significantly increases the internal stress within the films and simultaneously reduces the electrodepositing current efficiency. This study aims to mitigate the hydrogen evolution during electrodeposition of iron by using acetamide (C2H5NO) as additive. Electrochemical measurements conducted in this study reveal that the presence of C2H5NO molecules in the solution effectively hinders the electrochemical reduction of H+ ions, leading to an improvement in the current efficiency for iron electrodeposition, rising from 79 to 87%. Furthermore, analyses using X-ray Diffraction (XRD) and Scanning Electron Microscopy (SEM) clearly demonstrate that the addition of C2H5NO to the electrolyte solution significantly reduces the internal stress of the electrodeposited iron film from 442 to 74 MPa. This reduction, in turn, cause preference a smoother surface, eliminating the occurrence of cracks. Additional insights from Density Functional Theory (DFT) calculations reveal that C2H5NO molecules within the solution modify the electrode/solution interface by forming a robust and densely adsorptive layer, primarily composed of C2H5NO molecules, on the surface of the iron cathode. Moreover, it is noteworthy that C2H5NO molecules exhibit a preference for binding with H+ ions over H2O molecules, thus effectively obstructing the diffusion of H+ ions to the electrode surface within the solution. [ABSTRACT FROM AUTHOR]

The chemistry of condensed heterocyclic molecules in terms of their diverse biological properties and role in drug development has been the subject of numerous publications. Tetrazole is a naturally occurring chemical that has been used to create several commercially available drugs and as a result, plays an important role in pharmaceutical chemistry. The current study aimed to create and synthesize seven new 2,5-disubstituted-tetrazole-acetamide derivatives 3a-3g via an N-alkylation reaction of 5-(4-bromophenyl)-2H-tetrazole or 5-(4-chlorophenyl)-2H-tetrazole 1a,1b, and N-acetamide derivatives 2a-2f, and 2g in CH3CN using potassium carbonate as a base in good yields. New molecules were assigned based on nuclear magnetic resonance results (¹H, 13C NMR, and two-dimensional-NMR [heteronuclear single quantum coherence spectroscopy [HSQC]), along with mass spectrometry (EI-MS) techniques. The products' biological activities were confirmed using the tetrazolium (MTT) assay against MCF-7 (breast cancer) and PC3 (prostate cancer) cells and their effects on the normal hepatic cell line, WRL68. Results showed that compounds 3e-3g inhibited PC3 cells with average IC50 values of 32.59, 54.99, and 55.53 μM, respectively. Compounds 3a and 3b demonstrated cytotoxicity against the MCF-7 cell line, with average IC50 values of 94.25 and 68.16 μM, respectively. Compounds 3a, 3c, and 3e-3g on the 3ERT and 3ZK6 receptors demonstrated strong binding capabilities and improved protein interactions according to molecular docking experiments. [ABSTRACT FROM AUTHOR]

Two new [1-(phenyl­sulfon­yl)-1H-indol-2-yl]methanamine derivatives, namely, N-(3-methoxyphenyl)-N-{[1-(phenyl­sulfon­yl)-1H-indol-2-yl]methyl}acetamide, C24H22N2O4S, (I), and N-(2,5-di­meth­oxy­phen­yl)-N-{[1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}benzene­sulfonamide, C29H26N2O6S2, (II), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C—H⋯O bonding [C⋯O = 3.312 (4)–3.788 (8) Å], with the structure of II exhibiting a larger number, but weaker bonds of this type. Slipped π–π interactions of antiparallel indole systems are specific for I, whereas the structure of II delivers two kinds of C—H⋯π interactions at both axial sides of the indole moiety. These findings agree with the results of Hirshfeld surface analysis. The primary contributions to the surface areas are associated with the contacts involving H atoms. Although II manifests a larger fraction of the O⋯H/H⋯O contacts (25.8 versus 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations. [ABSTRACT FROM AUTHOR]

Src homology‐2 (SH2) domain‐containing phosphatase‐2 (SHP2), the first protooncogenic phosphatase is a key mediator in the development and progression of various cancers. Several allosteric sites have been identified in SHP2, inhibitors of which are being developed. In the current study, we have designed and synthesized a library of 21 thioacetamide‐tethered thiadiazole‐1,2,4‐triazole hybrids (compounds 16–36) and evaluated their in vitro SHP2 inhibitory potential. Compound 28 (N‐(5‐(benzo[d][1,3]dioxol‐5‐yl)‐1,3,4‐thiadiazol‐2‐yl)‐2‐((5‐(4‐methoxyphenyl)‐4H‐1,2,4‐triazol‐3‐yl)thio)acetamide) emerged as the most potent SHP2 inhibitor (IC50=0.318±0.001 μM) inhibiting the enzyme in a mixed to non‐competitive manner. In silico studies revealed that the lead inhibitor strongly binds to the tunnel allosteric site of SHP2. Further, cytotoxicity studies revealed that compound 28 caused death of SHP2‐driven MCF‐7 (GI50=37.02±0.25 μM) and U87MG cells (GI50=68.69±0.21 μM) in a dose‐dependent manner and inhibited MCF‐7 cell colony formation and migration. Flow cytometric analysis showed that it exerted its antiproliferative effect on U87MG cells by inducing early apoptosis (Q2 phase) and inhibiting cell cycle progression at the G1 and S phase. Compound 28 was shown to increase oxidative stress in the U87 cells by promoting ROS generation and loss of mitochondrial integrity. In summary, the present study produced a potent SHP2 inhibitor (compound 28) with a promising in vitro cytotoxicity profile, thus meriting further investigation. [ABSTRACT FROM AUTHOR]

AbstractThis study focused on the biodegradation of acetonitrile (ACN) and subsequent nitrification using a mesophilic microbial consortium isolated from Phragmites australis and Zantedeschia aethiopica plants which were in a nitrile-contaminated habitat. The organisms were identified using 16S rDNA sequencing and were determined to be Bacillus sp., Pseudomonas sp., and Enterobacter sp. organisms. These organisms were used as a consortium in the biodegradation of ACN. The physicochemical conditions including temperature, pH, and ACN concentration were optimized using response surface methodology (RSM). Based on this method, an optimal biodegradation efficiency of 99% was achieved at an optimized temperature of 34.99 °C, pH of 7:03, and an ACN concentration of up to 127.23 mg/L. These optimized parameters were used in the continuous operation over a period of 122 days with increased ACN concentrations of 150–500 mg/L where the biodegradation efficiency exceeded 99% which were accompanied by the production of acetic acid, acetamide, and nitrogenous compounds. Acetic acid and acetamide were completely utilized while total nitrogen (TN) was 1.2 mg/L on the last day of the study. [ABSTRACT FROM AUTHOR]

Context. The carbamoyl radical (H2NCO) is believed to play a central role in the ice-grain chemistry of crucial interstellar complex organic molecules such as formamide and acetamide. Yet, little is known about this radical, which remains elusive in laboratory gasphase experiments. Aims. In order to enable interstellar searches of H2NCO, we have undertaken a mandatory laboratory characterisation of its pure rotational spectrum. Methods. We report the gas-phase laboratory detection of H2NCO, produced by H-atom abstraction from formamide, using pure rotational spectroscopy at millimetre and submillimetre wavelengths. Millimetre-wave data were acquired using chirped-pulse Fourier-transform spectroscopy, while submillimetre-wave ones were obtained using Zeeman-modulated spectroscopy. Experimental measurements were guided by quantum-chemical calculations at the ωB97X-D/cc-pVQZ level of theory. Interstellar searches for the radical have been undertaken in the Protostellar Interferometric Line Survey (PILS) towards the solar-type protostar IRAS 16293-2422. Results. From the assignment and fit of experimental transitions up to 660 GHz, reliable spectroscopic parameters for H2NCO in its ground vibrational state have been derived, enabling accurate spectral predictions. No transitions of the radical were detected in the PILS survey. The inferred upper limit shows that the H2NCO abundance is at least 60 times below that of formamide and 160 times below that of HNCO in this source; a value that is in agreement with predictions from a physico-chemical model of this young protostar. [ABSTRACT FROM AUTHOR]

We describe herein a method for transition‐metal‐free (hetero)arylsulfonylation of 1‐iodopyrrolo[1,2‐a]quinoxalines with sodium arylsulfinates. The corresponding aryl iodides were in situ prepared from eletrophilic iodination of C1−H bonds in pyrrolo[1,2‐a]quinoxalines with N‐iodosuccinimide. The ensuing sulfonylation only required DMSO as solvent and completed after 15 min. Many arylsulfinates bearing chloro, bromo, methylsufonyl, acetamide, and nitro groups were competent substrates. Heteroarylsulfonylation of pyrrolo[1,2‐a]quinoxalines were also feasible. [ABSTRACT FROM AUTHOR]

A new automated radiosynthesis of [11C]2‐(2,6‐difluoro‐4‐((2‐(N‐methylphenylsulfonamido)ethyl)thio)phenoxy)acetamide ([11C]K2), a radiopharmaceutical for the glutamate α‐amino‐3‐hydroxy‐5‐methyl‐4‐isoxazole propionic acid (AMPA) receptor, is reported. Although manual syntheses have been described, these are unsuitable for routine production of larger batches of [11C]K2 for (pre)clinical PET imaging applications. To meet demands for the imaging agent from our functional neuroimaging collaborators, herein, we report a current good manufacturing practice (cGMP)‐compliant synthesis of [11C]K2 using a commercial synthesis module. The new synthesis is fully automated and has been validated for clinical use. The total synthesis time is 33 min from end of bombardment, and the production method provides 2.66 ± 0.3 GBq (71.9 ± 8.6 mCi) of [11C]K2 in 97.7 ± 0.5% radiochemical purity and 754.1 ± 231.5 TBq/mmol (20,382.7 ± 6256.1 Ci/mmol) molar activity (n = 3). Batches passed all requisite quality control testing confirming suitability for clinical use. [ABSTRACT FROM AUTHOR]

Non-annulated tetrazole-containing polynuclear compounds, in which heterocyclic fragments are bound by an acetamide linker were synthesized. The synthesis was accomplished by acylation of 2-hydrazinyl-4,6-dimethylpyrimidine, 4-amino-4H-1,2,4-triazol-3-thiol, 2-[(1-amino-1H-tetrazol-5-yl)thio]-N-tert-butylacetamide, 1-methyl-1H-tetrazol-5-amine, and 2-methyl-2H-tetrazol-5-amine with one key reagent, (5-phenyltetrazol-2-yl)acetyl chloride. Preliminary in silico studies showed the presence of the in vivo antidiabetic (diabetes 2 type) activity in N′-(4,6-dimethylpyrimidin-2-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetohydrazide. N-(3-Mercapto-4H-1,2,4-triazol-4-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetamide demonstrated minimal hypoglycemic activity in in vivo studies, at the same time, it showed pronounced activity as a drug for combating obesity. [ABSTRACT FROM AUTHOR]

Considering the escalating global prevalence and the huge therapeutic demand for the treatment of hypertension, there is a persistent need to identify novel target sites for vasodilator action. This study aimed to investigate the role of TRPA1 channels in carvacrol-induced vasodilation and to design novel compounds based on carvacrol structure with improved activities. In an isolated tissue bath experiment, it was shown that 1 µM of the selective TRPA1 antagonist A967079 significantly (p < 0.001) reduced vasodilation induced by 3 mM of carvacrol. A reliable 3D-QSAR model with good statistical parameters was created (R2 = 0.83; Q2 = 0.59 and R p r e d 2 = 0.84) using 29 TRPA1 agonists. Obtained results from this model were used for the design of novel TRPA1 activators, and to predict their activity against TRPA1. Predicted pEC50 activities of these molecules range between 4.996 to 5.235 compared to experimental pEC50 of 4.77 for carvacrol. Molecular docking studies showed that designed molecules interact with similar amino acid residues of the TRPA1 channel as carvacrol, with eight compounds showing lower binding energies. In conclusion, carvacrol-induced vasodilation is partly mediated by the activation of TRPA1 channels. Combining different in silico approaches pointed out that the molecule D27 (2-[2-(hydroxymethyl)-4-methylphenyl]acetamide) is the best candidate for further synthesis and experimental evaluation in in vitro conditions. [ABSTRACT FROM AUTHOR]

This article discusses the importance of protecting amines in organic synthesis to prevent unwanted side reactions, particularly in the synthesis of complex peptides, amino acids, and natural products. Various methods for amine protection are explored, including formylation, acetylation, alkylation, and the use of specific groups like Boc, Cbz, and Fmoc. The article introduces a new dicationic catalyst, [C4(Tr)2]·2Cl, for the N-Boc protection and acetylation of amines under solvent-free conditions. The catalyst is shown to be effective in producing N-tert-butylcarbamates and N-acetamides with high yields and minimal variation based on substituents. The method is selective and does not damage structural units like the methoxy group. The efficiency of this method is compared to other reported methods and is shown to have favorable reaction times, yields, and mild conditions. The catalyst is easily prepared, reusable, and environmentally friendly. The article provides detailed experimental procedures and characterization data for the catalyst and the synthesized compounds. The authors hope that this new catalyst will find further applications in synthesis. [Extracted from the article]

The work aims to develop a biopolymer-dextrin-based three-dimensional crosslinked hydrophilic material for antimicrobial delivery. The copolymer (Dxt-PNVA) has been prepared by in-situ grafting of poly(N-vinylacetamide), followed by cross-linking with N,N'-methylenebisacrylamide with dextrin. By varying the concentrations of the reactants, an optimized copolymer (Dxt-PNVA 5) with the lowest % of crosslinking has been chosen for biomedical applications. The copolymeric gel has been characterized in detail using various techniques, followed by its cytocompatibility study using HeLa Cell lines that confirm the cytocompatible nature of the material. Copolymeric gel is a suitable material for the effective release of two antimicrobials (amoxicillin trihydrate and ornidazole) from tablet formulation for a prolonged period of 24 h. The obtained data demonstrates that the cytocompatible hydrogel has the potential characteristics of a daily dose administration for amoxicillin trihydrate and ornidazole. [ABSTRACT FROM AUTHOR]

According to our preliminary study, melatonin and its N-amide derivatives (N-(2-(1-4-bromobenzoyl-5-methoxy-1H-indol-3-yl)ethyl)acetamide (BBM) and 4-bromo-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide (EBM)) inhibited the marker of acute inflammation in tests in vitro and in vivo. The anti-inflammatory agent is intended for the prevention and treatment of chemotherapy-induced toxicity. In this study aimed to evaluate the effect of melatonin and its derivatives on mechanisms related to chemotherapy-induced oral mucositis by in vitro ROS and 5-FU-induced human keratinocyte cells as well as in vivo oral mucositis model. In in vitro H2O2-induced HaCaT cells, BBM had the highest level of protection (34.57%) at a concentration 50 µM, followed by EBM (26.41%), and melatonin (7.9%). BBM also protected cells against 5-FU-induced to 37.69–27.25% at 12.5–100 µM while EBM was 36.93–29.33% and melatonin was 22.5–11.39%. In in vivo 5-FU-induced oral mucositis in mice, melatonin, BBM, and EBM gel formulations protected tissue damage from 5-FU similar to the standard compound, benzydamine. Moreover, the weight of mice and food consumption recovered more quickly in the BBM group. These findings suggested that it was possible to develop BBM and EBM as new therapeutic agents for the treatment of oral mucositis. [ABSTRACT FROM AUTHOR]

Mono‐ and dichloro acetamides were prepared via a hydrodechlorination reaction of trichloroacetamides under controlled electrochemical conditions. The reactions were carried out in an undivided cell with constant current flow using n‐Bu4NI as supporting electrolyte and methanol as solvent and proton source. Deuterodechlorination of trichloroacetamide was also successful when methanol‐d4 was used as solvent under identical electrochemical conditions. [ABSTRACT FROM AUTHOR]