Synthesis, Solvatochromic Analysis and Theoretical Studies of 3-((1H-benzo[d][1,2,3]triazole-1-yl)methyl)-4- phenylethyl -1H-1,2,4-triazole-5(4H)-thione (original) (raw)
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2021
Inhibitory activities of five derivatives of 1,2,3-triazole and isoxazole-linked pyrazole hybrids (A,B,C,D and D) were investigated on two bacteria cell lines E.coli (5R1R) and S.aureous (2XCT) to predict their potency and their use as antibacterial agents. Spartan’14 was used to optimized the compounds via Density functional theory to calculate the molecular descriptors of the studied ligands and a standard drug (Amoxicillin). All the ligands obey Lipinski rule except ligand E with higher molecular weight greater than 500g/mol. The band gap which explained the stability of the ligand-protein complex formed were observed to be lower than the standard with outstanding lower band gap from Ligand B and E, hence this two ligand is expected to have higher stability as compared to other ligands and the standard drug. The predicted affinities via docking studies for E.coli were -7.3kcal/mol, -8.5kcal/mol, -7.5kcal/mol, -7.9kcal/mol, -8.9 kcal/mol and S.aureous were -6.9kcal/mol, -7.8kcal/m...
Design and Synthesis of p-hydroxybenzohydrazide Derivatives for their Antimycobacterial Activity
Journal of the Korean Chemical Society, 2012
The main mycobacterial infection in human is tuberculosis caused by Mycobacterium tuberculosis. Tuberculosis is the leading infectious cause of death in the world. Therefore there is continuing and compelling need for new and improved treatment for tuberculosis. The entire logic towards design of new compounds containing 4-hydroxy-N'-(1,3-thiazoldin-2-yldene)benzohydrazide moiety is basically for superior antimycobacterial activity. The recent advances in QSAR and computer science have provided a systematic approach to design a structure of any compound and further, the biological activity of the compound can be predicted before synthesis. The 3D-QSAR studies for the set of 4-hydroxy-N'-(1,3-thiazoldin-2-yldene)benzohydrazide and their derivatives were carried out by using V-life MDS (3.50). The various statistical methods such as Multiple Linear Regression (MLR), Partial Least Square Regression (PLSR), Principle Component Regression(PCR) and K nearest neighbour (kNN) were used. The kNN showed good results having cross validated r 2 0.9319, r 2 for external test set 0.8561 and standard error of estimate 0.2195. The docking studies were carried out by using Schrodinger GLIDE module which resulted in good docking score in comparison with the standard isoniazid. The designed compounds were further subjected for synthesis and biological evaluation. Antitubercular evaluation of these compounds showed that (4.a), (4.d) and (4.g) found as potent inhibitor of H37RV.
A green and efficient protocol has been developed for the synthesis of novel 1,2,3-triazole-chromene conjugates (7 a-j) via ultrasound assisted and NaHCO 3 catalyzed for the first time. Structures of all the new conjugates were deduced by various spectroscopic techniques. The newly synthesized triazolechromene conjugates were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain. The conjugates 7 f and 7 h were found to be most active with MIC value 12.5 μg/mL. Furthermore, all the conjugates were screened for their antioxidant activity and are highly active (IC 50 = 7.05-14 μg/mL) than the reference drug BHT (16.47 μg/mL). The triazole-chromene conjugates were also screened for their in vitro antifungal activity and some of e, 7 f and 7 i were exhibited potent activity (MIC = 6.25-25 μg/mL) than the reference drug Miconazole. Docking studies showed significant binding affinity in the active site of Mycobacterium tuberculosis DprE1 enzyme.
ACS Omega
A new series of 1,2,3-triazole hybrids containing either 2-or 4-hydroxyphenyl benzothiazole (2-or 4-HBT) and naphthalen-1-ol or 8-hydroxyquinoline (8-HQ) was synthesized in high yields and fully characterized. In vitro DNA binding studies with herring fish sperm DNA (hs-DNA) showed that quinoline-and 2-HBT-linked 1,2,3-triazoles of shorter alkyl linkers such as 6a are better with a high binding affinity (3.90 × 10 5 L mol −1) with hs-DNA as compared to naphthol-and 4-HBT-linked 1,2,3-triazoles bound to longer alkyl linkers. Molecular docking of most active 1,2,3-triazoles 6a−f showed high binding energy of 6a (−8.7 kcal mol −1). Also, compound 6a displayed considerable antibacterial activity and superior antifungal activity with reference to ciprofloxacin and fluconazole, respectively. The docking results of the fungal enzyme lanosterol 14-α-demethylase showed high binding energy for 6a (−9.7 kcal mol −1) involving dominating H-bonds, electrostatic interaction, and hydrophobic interaction. The absorption, distribution, metabolism, and excretion (ADME) parameter, Molinspiration bioactivity score, and the PreADMET properties revealed that most of the synthesized 1,2,3-triazole molecules possess desirable physicochemical properties for druglikeness and may be considered as orally active potential drugs. The electrophilicity index and chemical hardness properties were also studied by density functional theory (DFT) using the B3LYP/6-311G(d,p) level/basis set.
Journal of Molecular Structure, 2017
N-[2-(2-bromophenyl)-1,3-benzoxazol-5-yl]-2-phenylacetamide (NBBPA) was synthesized in this study as an original compound in order to evaluate its antibacterial activity against representative Gram-negative and Gram-positive bacteria, with their drug-resistant clinical isolate. Microbiological results showed that this compound had moderate antibacterial activity. Study also encompassed detailed FT-IR, FT-Raman and NMR experimental and theoretical spectroscopic characterization and assignation of the ring breathing modes of the mono-, ortho-and tri-substituted phenyl rings is in agreement with the literature data. DFT calculations were also used to identify specific reactivity properties of NBBPA molecule based on the molecular orbital, charge distribution and electron density analysis, which indicated the reactive importance of carbonyl and NH 2 groups, together with bromine atom. DFT calculations were also used for investigation of sensitivity of the NBBPA molecules towards the autoxidation mechanism, while molecular dynamics (MD) simulations were used to investigate the influence of water. The molecular docking results suggest that the compound might exhibit inhibitory activity against GyrB complex.
Heliyon, 2021
Quantum chemical calculation, performance of selective antimicrobial activity using molecular docking analysis, RDG and experimental (FT-IR, FT-Raman) investigation of 4-[{2-[3-(4-chlorophenyl)-5-(4-propan-2-yl) phenyl)-4, 5-dihydro-1H-pyrazol-1-yl]-4-oxo-1, 3-thiazol-5(4H)-ylidene} methyl] benzonitrile
Synthesis, molecular docking and antimicrobial evaluation of novel benzoxazole derivatives
Medicinal Chemistry Research, 2016
In this research, previously and newly synthesized 5-amino-2-(4-substitutedphenyl/benzyl)benzoxazoles (3a-3l) and 2-substituted-5-(4-nitro/aminophenylsulfonamido)benzoxazoles (5a-5l, 6a-6l) were evaluated for their antimicrobial activities against Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212 and Mycobacterium tuberculosis H37RV ATCC 27294 and their drug-resistant isolates Candida albicans ATCC 10231 and Candida krusei ATCC 6258. The chemical structures of the newly synthesized compounds were characterized by IR, 1 H NMR, 13 C NMR, LC-MS and elemental analysis. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at the minimum inhibitory concentration (MIC) values between 256 and 8 lg/mL. Compounds 3a, 3c and 3f exhibited significant antimycobacterial activity showing MIC value of 8 lg/mL against both M. tuberculosis and its drug-resistant isolate. InhA, the enoyl-acyl carrier protein reductase from M. tuberculosis, is one of the key enzymes in the FASII system involved in mycobacterial fatty acid elongation cycle, which has been validated as an effective antimicrobial target. Molecular docking into active site of InhA was performed on 3FNE.PDB file to understand ligandprotein interactions. The compounds obtained from this research can be used as scaffolds in the design of new potent drugs.
Spectroscopy Letters, 2019
The theoretical parameters such as optimized geometrical parameters (bond lengths, bond angles, and dihedral angles), vibrational assignments, non-linear optical property, natural population analysis, and global chemical descriptors were calculated using the density functional theory with Becke, 3-parameter, Lee-Yang-Parr functional and Coulomb-attenuating method. Spectroscopic characterization of (E)-N 0-((1H-Indol-3-yl)methylene)-4-bromobenzohydrazide was investigated by the Fourier transform infrared analysis with the potential energy distribution, proton nuclear magnetic resonance, and ultraviolet-visible techniques. The intermolecular interactions of the title molecule in the crystal structure were visualized by the three-dimensional Hirshfeld surface and associated two-dimensional fingerprint plots. In order to understand molecular stability, global reactive properties calculated at the time-dependent density functional theory have been investigated by visualization of frontier molecular orbitals. In addition, the first-order hyperpolarizability has been investigated to understand the non-linear optical activity of the molecule. Molecular docking studies supporting the antibacterial activity of the title molecule give a high-binding energy value of À5.20 kcal/mol due to the interaction of the carbonyl group with the target protein.
Brazilian Journal of Physics, 2018
The novel compound 3′-(1-benzyl-5-methyl-1H-1,2,3-triazole-4-carbonyl)-4′-(4-bromophenyl)-1′-methyl-2H-spiro [acenaphthylene-1,2′-pyrrolidine]-2-one (BTBANP) is synthesized and characterized by FT-IR/Raman, 1 H-NMR, 13 C-NMR, fluorescence, UV-Vis, and single-crystal X-ray diffraction. The molecular structure of BTBANP in the ground state is optimized using density functional theory (DFT/B3LYP) method with 6-311G (d, p) basis set and compared with the experimental data. Kurtz powder technique is employed to determine the non-linear optical (NLO) effect of BTBANP and thus the charge delocalization and stability of the compound are discussed. The efficiency of second-harmonic generation (SHG) of BTBANP is 1.53 times more than that of potassium dihydrogen phosphate (KDP). DFT/B3LYP/6-311G (d, p) technique is also utilized to compute NLO, NBO, HOMO-LUMO, global chemical descriptors, and thermodynamic properties at different temperatures. The molecular docking study of BTBANP reveals good inhibitory activity against topoisomerase II and lanosterol 14 α-demethylase enzymes.