Design, Synthesis, and Characterization of Novel Substituted Dihydrooxazoles: Biological Evaluation and Molecular Docking

Rao, A. Tejeswara; Naveen, Kanagaraj; Mutyalanaidu, G.; Venkanna, Boda; Anireddy, Jaya Shree

doi:10.1134/s1070428022010183

Cited by 2 publications

(1 citation statement)

References 25 publications

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“…The binding model of these ligands with Staphylococcus aureus gyrase complex-DNA synthetase protein (2XCT) was simulated using the Autodock program to validate the antimicrobial activity (Table 2, Figure 2) [53,54]. Accordingly, the micro bacterial stabilizing and the cocrystallized ligands were docked into the twinned 3.35A structure of Staphylococcus aureus Gyrase complex with Ciprofloxacin and DNA (PDB: 2XCT) [55][56][57]. The graphical user interface AutodockTools (1.5.6rc3) was performed to setup every inhibitor enzyme interaction where all hydrogen atoms were added, gasteiger charges were calculated and nonpolar hydrogen atoms were merged to carbon atoms.…”

Section: Docking Analysismentioning

confidence: 99%

Synthesis, antimicrobial activity, and in silico studies of fluoroquinolones bearing 1,3,4‐oxadiazolyl‐triazole derivatives

Venkateswara Rao,

Allaka,

Gandla

et al. 2023

Journal of Heterocyclic Chem

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Compounds containing fluoroquinolone (FQ) moiety occupy privileged chemical space for discovering novel bioactive substances. In continuation of our research work, a new series of FQs linked to triazolyl–thiadiazine hybrids (3a–f) and triazolyl–oxadiazoles (5a–f) were developed as a new antimicrobial agent targeting DNA gyrase of Staphylococcus aureus. All the novel compounds have been characterized with IR, 1H NMR, 13C NMR, mass spectral analysis and elemental analysis. All the synthesized derivatives were investigated for their antibacterial effect against various bacterial and fungal strains. Against Gram‐positive bacteria S. aureus, compounds 3e, 5a, and 5d showed the highest antibacterial activity with minimum inhibitory concentrations (MIC) values 5.0 ± 0.04, 8.6 ± 0.03, and 6.1 ± 0.02 μg/mL, respectively. FQ derivatives 3a, 5c had the most potent antibacterial activity against Klebsiella pneumonia bacteria with MICs 6.4 ± 0.01, 4.1 ± 0.01 μg/mL and compounds 3e, 5d are active against Gram‐negative bacteria Bacillus cereus with MICs 8.3 ± 0.02, 10.0 ± 0.02 μg/mL, respectively. Interestingly, the molecules 3e were slightly more selective towards antifungal activity against Fusarium oxysporum (MIC 4.2 ± 0.01 μg/mL), compared to fluconazole (MIC 3.5 ± 0.01 μg/mL). In addition, a fascinating molecular modeling investigation showed that our FQs 3, 5 demonstrated good binding inhibition of S. aureus complex in DNS gyrase (2XCT) towards advancing an efficient medication against antibacterial disease. The prepared ligand 3c forms three hydrogen bonds with amino acid residues LysB:1043 (N23…NZ), ArgB:1092 (O20…NH), GlyB:1082 (O…N) with bond lengths 3.13, 2.15, 2.76 A°, respectively.

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