Synthesis, characterization, spectroscopic properties, theoretical calculation, and antimicrobial activity of new aryldisulfonamides

WOS: 000289965000004New aryldisulfonamides were synthesized and characterized by FTIR, (1)H NMR, (13)C NMR, HETCOR, COSY, LC-MS and elemental analysis techniques. The compounds gave intense emissions, where lambda(max) = 405, 379 and 402 nm, upon irradiation by Ultra-Violet light. The photoluminescence quantum yields and long excited-state lifetimes of the compounds were calculated and were found to have photoluminescence quantum yields 39 +/- 1.8%, 45 +/- 2.2% and 34 +/- 1.4% and long excited-state lifetimes of 3.65 +/- 0.16, 4.17 +/- 0.20 and 3.15 +/- 0.12 ns, respectively. The photoluminescence intensities and quantum yields of compounds varied with the position of substituent on the ring and the chain length between aromatic rings. These novel compounds may be of interest as organic emitting materials for electroluminescent devices. The visible absorption maxima were calculated using time-depended density-functional theory (ID-OFT) and Zerner's intermediate neglect of differential overlap/spectroscopic (ZINDO/S) method in the gas phase. Further, the compounds were evaluated for in vitro antimicrobial activity against various microorganisms by microdilution and disk diffusion methods. (C) 2011 Elsevier B.V. All rights reserved.TUBITAKTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TBAG 104 T 390, MAG 104M 367]; Gazi University Scientific Research ProjectGazi University [05/2008-05]The authors wish to thank TUBITAK for the financial support (TBAG 104 T 390 and (MAG 104M 367) and Gazi University Scientific Research Project (05/2008-05). We would also like to thank the Departments of Chemistry at Gazi University and Gaziantep University

Acetohydroxyacid Synthase (AHAS) Inhibitor-Based Commercial Sulfonylurea Herbicides as Glutathione Reductase Inhibitors: in Vitro and in Silico Studies

In this study, in vitro inhibitory effect of AHAS inhibiting-based commercial sulfonylurea herbicides on human GR and S. cerevisiae GR was determined by electrochemical method. Our findings, the first report in literature, show that the four commercial herbicides were found to be the inhibitors in the range of 4.90–9.75 μM for ScGR, and in the range of 8.54–18.84 μM for hGR. Global reactivity descriptors (energy gaps, electronegativity, hardness and electrophilicity index) of the herbicides were calculated by DFT/B3LYP/6-31G(d,p) method in gas phase. The electrochemical behavior of the herbicides was studied by cyclic voltammetry. Single-electron half-wave reduction potentials and global reactivity descriptors were correlated with the IC50 values of the herbicides. Molecular docking analysis using Schrödinger Suite was applied to examine the interaction between the herbicides and human GR (PDB ID:1XAN and 2GH5), S. cerevisiae GR (PDB ID:2HQM), P. falciparum GR (PDB ID:1ONF), C. albicans AHAS (PDB ID:6DEL) and ScAHAS (PDB ID: 5FEM. Based on the docking results, it can be predicted that (a) herbicides have similar binding potential to two different binding sites of hGRs, (b) herbicides may have antimalarial potential against P. falciparum (c) herbicides may have antifungal potential against C. albicans. © 2022 Wiley-VCH GmbH

Synthesis of benzimidazole derivatives containing amide bond and biological evaluation as acetylcholinesterase, carbonic anhydrase I and II inhibitors

Acetylcholinesterase (AChE) and carbonic anhydrase I (CA-I) and II (CA-II) are two vital metabolic enzymes. AChE inhibitors are seen as target molecules in drug development studies for Alzheimer's treatment. CA inhibitors are target molecules for treating many diseases from glaucoma to cancer. For this reason, it is crucial to identify new AChE and CA inhibitors. In this study, four benzimidazole acetamide derivatives were synthesized and their inhibition effects were investigated against human erythrocyte carbonic anhydrase I (hCA-I), II (hCA-II), and AChE. IC50 values of 9a-10b were determined in the range of 0.936 to 17.07 µM for AChE. IC50 values of 9a–10b for hCA-I were found as 7.21 µM, 4.72 µM, 6.08 µM, 8.23 µM, respectively. On the other hand, IC50 values of 9a–9b for hCA-II were found as 8.64 µM, 7.07 µM, 4.12 µM, 5.93 µM, respectively. According to IC50 values, 9a–10b molecules exhibited strong inhibition effects for AChE and hCAI, II. Also, Molecular docking studies were carried out to explain the binding interaction of 9a–10b with AChE, hCA-I, and hCA-II. © 202

In vitro anti-leishmanial activities and structure-activity relationship analysis of new antimony(III) complexes

1609-1617New fourteen antimony(III) complexes of general formula [SbLnCl3] (where n= 1 or 2, L =2-aminopyridine, 5-methyl-2-aminopyridine, 2-aminopyrimidine, 4,6-dimethoxy-2-aminopyrimidine, 2-benzyl-2-thiopseudeourea,2-guanidinobenzimidazole, 2-amino-5-thiol-4,6-dimethoxypyrimidine, 2-amino-5-(1H-tetrazol-5-ylthio)-4,6-dimethoxypyrimidine, N-2-pyrimidine, 2-piperidinecarboxamide, N-2-pyrimidine, 2-pyrrolidinecarboxamide, 2-amino-5-(1H-tetrazol-5-iltiyo)-4,6-dimethoxypyrimidine-2-pyrrolidinecarboxamide and N-2-pyrimidine, 5-chloro-2-thiophenecarboxamide, N-2-benzothiazol-2-pyrrolidinecarboxaamide, N,N-(1,2-phenyl)dipyrrolidine-2-carboxamide) have been synthesized and their anti-leishmanial activity have been assessed in vitro against Leishmania tropica promastigotes. The best complex, Sb(2-guanidinobenzimidazole)Cl3 is demostrated 3.16% growth inhibition at a concentration of 31.25 μg/mL. In general, antimony(III) complexes containing pyrimidine ligands has showed higher anti-leishmanial activity than antimony(III) complexes bearing pyridine ligands, and electron-donating substituents decrease the anti-leishmanial activity. All complexes have been optimised with DFT/B3LYP/LANL2DZ method in the gas phase. Several descriptors are tested to find a quantitative correlation between anti-leishmanial activity and structural properties of the complexes by best multiple linear regression method. Good correlations are obtained with minimum net atomic charge for a C atom and maximum bond order of a Cl atom. The developed QSAR equation is internally validated

Synthesis, crystal structure, antibacterial activities, and electrochemical studies of new N,N '-polymethylene bis-sulfonamides

WOS: 000301606200001Four disulfonamide derivatives (C2H5 center dot SO2 center dot NH)(2)(CH2)(n) (n = 2, 3, 4, 5) were synthesized and characterized by FTIR, H-1 NMR, C-13 NMR, HETCOR, LCMS and elemental analysis.Ethanesulfonamide-N,N'-pentamethylene bis was also characterized by X-ray single crystal diffraction measurement. The electrochemical characteristics of the disulfonamide derivatives were performed by cyclic voltammetry and chronoamperometry. H-1 and C-13 NMR chemical shifts of the compounds were calculated by using DFT-/B3LYP methods with a 6-311++G (d,p) basis set. Antibacterial activity and the structural relationship of the compounds showed that activity decreases proportionately to the increasing length of the carbon chain between NH groups, log P values, hydration energy and molecular volumes. Anodic peak potentials and HOMO values do not correlate with the activity, but reduction potential and LUMO decrease weakly with increasing activity. (C) 2011 Elsevier B.V. All rights reserved.TUBITAKTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [104T390]; Gazi University BAPGazi University [05/2006-33]This research was supported by TUBITAK Research Fund under Project No.: 104T390, Gazi University BAP (No. 05/2006-33)

In vitro anti-leishmanial activities and structure-activity relationship analysis of new antimony(III) complexes

New fourteen antimony(III) complexes of general formula [SbLnCl3] (where n= 1 or 2, L =2-aminopyridine, 5-methyl-2-aminopyridine, 2-aminopyrimidine, 4,6-dimethoxy-2-aminopyrimidine, 2-benzyl-2-thiopseudeourea,2-guanidinobenzimidazole, 2-amino-5-thiol-4,6-dimethoxypyrimidine, 2-amino-5-(1H-tetrazol-5-ylthio)-4,6-dimethoxypyrimidine, N-2-pyrimidine, 2-piperidinecarboxamide, N-2-pyrimidine, 2-pyrrolidinecarboxamide, 2-amino-5-(1H-tetrazol-5-iltiyo)-4,6-dimethoxypyrimidine-2-pyrrolidinecarboxamide and N-2-pyrimidine, 5-chloro-2-thiophenecarboxamide, N-2-benzothiazol-2-pyrrolidinecarboxaamide, N,N-(1,2-phenyl)dipyrrolidine-2-carboxamide) have been synthesized and their anti-leishmanial activity have been assessed in vitro against Leishmania tropica promastigotes. The best complex, Sb(2-guanidinobenzimidazole)Cl3 is demostrated 3.16% growth inhibition at a concentration of 31.25 μg/mL. In general, antimony(III) complexes containing pyrimidine ligands has showed higher anti-leishmanial activity than antimony(III) complexes bearing pyridine ligands, and electron-donating substituents decrease the anti-leishmanial activity. All complexes have been optimised with DFT/B3LYP/LANL2DZ method in the gas phase. Several descriptors are tested to find a quantitative correlation between anti-leishmanial activity and structural properties of the complexes by best multiple linear regression method. Good correlations are obtained with minimum net atomic charge for a C atom and maximum bond order of a Cl atom. The developed QSAR equation is internally validated

Biological activities and DNA interactions of aqueous extract of Phlomis linearis (Boiss. & Bal.)

Phlomis linearis Boiss. & Bal. of the Lamiaceae family is one of the endemic species in Turkey, i.e., growing in the east, central, and southeast parts of Anatolia and used for herbal tea. This study was designed to identify the biochemical and bioactivity properties of this endemic species by DPPH scavenging activity, metal chelating activity, total phenolic content, HPLC-DAD analysis, and MTT assay. Furthermore, the plant extract was evaluated for its antimicrobial activity against bacteria and fungi by using the microdilution method. The interactions between extract and plasmid DNA and their restriction endonuclease reactions were investigated by agarose gel electrophoresis. To support our hypothesis, we performed a molecular docking analysis. The DPPH scavenging activity of the plant extract was 53.86 ± 0.50 µg/ml in terms of IC50 value. The IC50 value of the plant extract was determined as 14.71 ± 4.01 mg/ml for metal chelating assay. The phenolic content of the extract was 231.55 ± 2.11 mg/g dry weight expressed as gallic acid equivalents (GAE). HPLC-DAD results revealed that the phenolic compounds were mainly derivatives of rosmarinic acid, chlorogenic acid, luteolin, luteolin-7-glycoside, luteolin derivatives, rutin derivatives, and apigenin derivatives. Besides, the cytotoxic activity of the plant extract against L929 fibroblast, H1299 non-small-cell lung carcinoma, and Caco-2 colorectal adenocarcinoma cell lines was determined by MTT assay. Phenolic content and molecular docking results correlated with each other

Aromatic sulfonyl hydrazides and sulfonyl hydrazones: antimicrobial activity and physical properties

A series of novel aromatic sulfonamide derivatives (1-7) were synthesized and characterized by elemental analyses, FT-IR, H-1 NMR, C-13 NMR, and LC/MS techniques. The compounds' quantum mechanical descriptors, surface area, and molecular volume were calculated. All the synthesized compounds were evaluated in vitro as antimicrobial agents against representative strains of gram-positive and gram-negative bacteria and as antifungal agents for yeast by both the disc diffusion and minimal inhibition concentration methods for comparison. All the bacteria and fungi studied were screened against some commercial antibiotics to compare with our chemicals' zone diameters. Quantitative structure-activity relationship studies with multiple linear regression analysis were applied to find the correlation between the different calculated molecular descriptors of the synthesized compounds and biological activity

Synthesis, characterization and antimicrobial activity of new butanesulfonamides

WOS: 000248688400281

Experimental and theoretical studies on methanesulfonic acid 1-methylhydrazide: Antimicrobial activities of its sulfonyl hydrazone derivatives

WOS: 000272896300009Methanesulfonic acid 1-methylhydrazide (msmh) and its sulfonyl hydrazone derivatives, salicylaldehyde-N-methylmethanesulfonylhydrazone (salmsmh) and 2-hydroxy-1-naphthaldehyde-N-methylmethanesulfonylhydrazone (nafmsmh) were synthesized and characterized by using FT-IR, H-1 NMR, C-13 NMR, LC-MS and elemental analysis Conformation analysis of msmh based on DFT/B3LYP/6-311G(d) method was performed. H-1 and C-13 shielding tensors of msmh for the most stable conformer were calculated with GIAO/DFT/B3LYP/6-311++G(2d, 2p) methods in vacuo, and various solvents such as DMSO, THF, acetonitrile, methanol and aqueous solution. The harmonic vibrational wavenumbers for the most stable conformer were calculated using at B3LYP/6-311G(d) level Antimicrobial activity of the compounds was also screened against Gram-positive bacteria (Staphylococcus aureus ATCC 25923. Bacillus cereus RSKK 863)and Gram-negative bacteria(Escherichia coli ATCC 11230, Salmonella enterititis ATCC 40376, Pseudomonos aeruginosa ATCC 28753) by both disc diffusion and micro dilution methods. (C) 2009 Elsevier B.V. All rights reservedTUBITAKTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [104 T 390]; Gazi University BAPGazi University [05/2005-59]The authors thank the TUBITAK (Grant No 104 T 390) and Gazi University BAP (Grant No. 05/2005-59) for the financial support of this project