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Synthesis, antimicrobial activity, and in silico studies of fluoroquinolones bearing 1,3,4‐oxadiazolyl‐triazole derivatives
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 antimicr...
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Published in: | Journal of heterocyclic chemistry 2023-10, Vol.60 (10), p.1666-1683 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | 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,
1
H NMR,
13
C 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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ISSN: | 0022-152X 1943-5193 |
DOI: | 10.1002/jhet.4700 |