Synthesis and antitumor activity of 3-(5-benzylidenethuzolo-triazlone)fluoroquinolones
10.11665/j.issn.1000-5048.20180605
- VernacularTitle:3-(5-苄叉基噻唑并均三唑酮)氟喹诺酮类化合物的合成及其抗肿瘤活性
- Author:
Yaling JIANG
1
;
Ke LI
;
Wenlong HUANG
;
Guoqiang HU
Author Information
1. 郑州工业应用技术学院药物化学教研室
- Publication Type:Journal Article
- Keywords:
fluoroquinolone;
s-triazole;
thiazole;
thiazolotriazole;
unsaturated ketone;
synthesis;
antitumor activity
- From:
Journal of China Pharmaceutical University
2018;49(6):671-675
- CountryChina
- Language:Chinese
-
Abstract:
To discover an efficient approach for the conversion of antibacterial fluoroquinolones into an antitumor activity, a fused heterocycle ring core, thiazolo［3, 2-b］［1, 2, 4］triazol-5-one was used as an isostere and further modified with an arylidene group. Then, 12 novel C-3 fused heterocyclic unsaturated ketones, 1- ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-3-［6-arylidene-thiazolo［3, 2-b］［1, 2, 4］triazol-5(6H)-one-3-yl］- quinolon-4(1H)-ones(6a-6l), were designed and synthesized from pefloxacin(1). The structures were characterized by elemental analysis and spectral data, and the in vitro antitumor activity of the title compounds against SMMC-7721, Capan-1 and HL60 cell lines was evaluated. The preliminary pharmacological results demonstrated that the title compounds exhibited more significantly antiproliferative activity than the parent 1. The compounds with fluorophenyl or o-methoxyphenyl showed comparable activity to the comparasion doxorubicin. Thus, it appears to be an alternative route for a fused heterocyclic unsaturated ketone as an isostere of the C-3 carboxylic group to improve the antitumor activity.
