Synthesis and antitumor activities of fluoroquinolone C-3 isosteres(VIII):s-triazole sulfide-one thiosemicarbazone derivatives from pefloxacin
10.11665/j.issn.1000-5048.20150405
- VernacularTitle:培氟沙星C-3羧基等排体的合成及抗肿瘤活性(Ⅷ).均三唑硫醚酮缩氨基硫脲衍生物
- Author:
Yusuo XIE
1
;
Liuzhou GAO
;
Qiang YAN
;
Shumin WU
;
Lili NI
;
Wenlong HUANG
;
Hui ZHAO
;
Guoqiang HU
Author Information
1. 河南大学化学生物学研究所
- Publication Type:Journal Article
- Keywords:
pefloxacin;
s-triazole;
sulfide-one;
thiosemicarbazone;
antitumor activity
- From:
Journal of China Pharmaceutical University
2015;46(4):416-420
- CountryChina
- Language:Chinese
-
Abstract:
To improve the antitumor activity of fluoroquinolones for a promising development of druggability, twelve novel fluoroquinolone C-3 s-triazole sulfide-one thiosemicarbazone derivatives(6a-6l)were designed and synthesized with a functionalized sulfide-one thiosemicarbazone as a modified side-chain for the C-3 bioisteric s-triazole ring of pefloxacin(1). The structures were characterized by elemental analysis and spectral data。The in vitro antitumor activity of novel compounds against SMMC-7721, L1210 and HL60 cell lines was evaluated. The preliminary pharmacological results demonstrated that the title compounds exhibited more significantly antiproliferative activity than either the parent 1 or the corresponding sulfide-one intermediates(5a-5l). In particular, compounds bearing a hydroxyl group or a fluorine atom attached to benzene ring were comparable to the control doxorubicin with an IC50 value of micro-molar concentration, respectively. It suggests that an azole ring modified with functional side-chain instead of the C-3 carboxylic group is favorable to the improve ment of antitumor activity.
