Premium
Design, Synthesis and In Vitro Anti‐mycobacterial Activities of 8‐ OMe Ciprofloxacin‐1 H ‐1,2,3‐triazole‐isatin‐(thio) Semicarbazide/Oxime Hybrids
Author(s) -
Xu Zhi,
Song Xufeng,
Hu Yuanqiang,
Qiang Min,
Lv Zaosheng
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3024
Subject(s) - semicarbazide , chemistry , thio , ciprofloxacin , cytotoxicity , in vitro , oxadiazole , isatin , triazole , vero cell , minimum inhibitory concentration , stereochemistry , antibiotics , biochemistry , organic chemistry
A series of novel 8‐OMe ciprofloxacin (8‐OMe CPFX)‐1 H ‐1,2,3‐triazole‐isatin‐(thio) semicarbazide/oxime hybrids 6a – l with the capacity to form hydrogen bond were designed, synthesized, and evaluated for their in vitro anti‐mycobacterial activities against Mycobacterium tuberculosis (MTB) H 37 Rv and MDR‐TB as well as cytotoxicity. All the synthesized hybrids (MIC: 0.39–16 μg/mL) exhibited excellent activities against MTB H 37 Rv and MDR‐TB, and the majority of them were more potent than the parent 8‐OMe CPFX (MIC: 1.56 and 2.0 μg/mL, respectively). In particular, the most active conjugate 6h (MIC: 0.39 and 1.0 μg/mL, respectively) was two to eight times more potent in vitro than the references CPFX (MIC: 3.12 and 4.0 μg/mL, respectively) and 8‐OMe CPFX against the tested strains and was comparable with or 64‐folds more potent than RIF (MIC: 0.39 and 64 μg/mL, respectively) against MTB H 37 Rv and MDR‐TB, respectively. In addition, all conjugates (CC 50 : 16–64 μg/mL) showed acceptable cytotoxicity, although most of them were more toxic than the parent (CC 50 : 64 μg/mL) in VERO cell line.