Synthesis, structural, spectral and antibacterial activity of 3,3a,4,5-tetrahydro-2H-benzo[g]indazole fused carbothioamide derivatives as antibacterial agents

Murugavel, S.; Deepa, S.; Ravikumar, C.; Raja, R.; Alagusundaram, Ponnusamy

doi:10.1016/j.molstruc.2020.128961

Cited by 13 publications

(5 citation statements)

References 30 publications

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“…Like L1, L2 formed pi-cations and amide-pi bonds with LYS47A, ILE39A, and GLY43B, where the distances were 3.73, 4.34, and 3.54 Å. L2 also formed seven pi-alkyl bonds with ALA44A (5.19 Å), LYS47A (4.35 Å), ALA44B (3.95 Å), LYS47B (4.98 Å), PRO52A (5.04 Å), ALA40B (4.67 Å), and ILE139B (4.24 Å), respectively. Results of docking studies revealed that L1 and L2 formed bonds to the active site of tyrosinase and showed strong interactions with Tyr267A, Ala40A, Ala44A, ALA44B, and Lys47B of the tyrosinase enzyme (PDB ID: 4j6u), which are in close vicinity to the control arbutin and support the literature [ 100 , 101 , 102 ].…”

Section: Resultssupporting

confidence: 85%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1E)-1-(thiophen-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L1) and N’2, N’6-bis[(1E)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2, 6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, 1H, and 13C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311+ G (d, p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of ∆H, ∆S, and ∆G for both the ligands. The optimized vibrational frequency and (1H and 13C) NMR obtained by B3LYP/cc-pvdz/6-311 + G (d, p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from Bacillus megaterium. The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against Bacillus megaterium with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol−1, respectively, with tyrosinase from Bacillus megaterium.‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬

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Section: Resultssupporting

confidence: 85%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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“…29 The binding energies for L with 1KZN were −7.7 kcal mol −1 , whereas the binding energy for Cipro-oxacin was reported −9.2 kcal mol −1 . 38 In L-1KZN, L formed two conventional hydrogen bonds (2.63 and 3.00 Å) of O-H-O-C with active site residues GLU50 and THR165. Pi-anion, pi-sigma and pi-alkyl bonds were also noticed with GLU50 (4.23 Å), VAL43 (4.62 Å), ALA47 (5.43 Å), VAL71 (5.47 Å), ILE78 (5.07 Å), VAL167 (5.06 Å), PRO79 (4.82 Å), and THR165 (3.75 Å) respectively.…”

Section: Molecular Docking Analysismentioning

confidence: 99%

Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

et al. 2023

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“…These methods aim to achieve an ideal conformation of the interaction between the ligand and receptor. The compounds containing pyrazole, thiophene, and 1,2,3‐triazole rings in their molecular structures (Figure 2) have been found to possess higher binding energies on the protein of E. coli bacteria with excellent molecular docking and ADME profiles [39–45] …”

Section: Introductionmentioning

confidence: 99%

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Sherashiya,

Kanjariya,

Naliapara

et al. 2024

ChemistrySelect

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To achieve environmentally benign synthesis and develop pharmacologically active compounds, a library of novel thiophene‐clubbed pyrazole‐1,2,3‐triazole hybrids was designed and successfully synthesized using L‐ascorbic acid as a green acid catalyst and ethanol as a green solvent. The reaction was carried out using microwave and ultrasonic irradiation methods to achieve a highly efficient reaction route. All title compounds were characterized and evaluated for their potential in vitro antimicrobial activity using Ciprofloxacin and Nystatin as standard drugs, in which compounds with chloro and naphthyl substitutions exhibited excellent antibacterial activity at concentrations of 25 μg/mL and compounds with methyl and methoxy substitutions exhibited excellent antifungal activity at concentrations of 100 μg/mL. Additionally, the molecular docking study showed that all compounds examined had excellent binding energies ranging from −9.3 to −10.3 kcal/mol, and naphthyl substitution displayed the highest binding energy (−10.3 kcal/mol) on the target protein of E. coli DNA gyrase subunit B. Furthermore, the final moieties were evaluated for in silico ADMET prediction to examine their drug‐likeness profile and toxic effects. The present study revealed that this structural information will be helpful in future antimicrobial drug design and development.

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Synthesis, structural, spectral and antibacterial activity of 3,3a,4,5-tetrahydro-2H-benzo[g]indazole fused carbothioamide derivatives as antibacterial agents

Cited by 13 publications

References 30 publications

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

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