Synthesis and antitumor activity of pefloxacin C-3 (rhodanine unsaturated ketone) amide derivatives
10.11665/j.issn.1000-5048.20170506
- VernacularTitle:培氟沙星C-3(绕丹宁不饱和酮)酰胺的合成及抗肿瘤活性
- Author:
Tong YANG
1
;
Xuemeng WANG
;
Rui WANG
;
Wenlong HUANG
;
Guoqiang HU
Author Information
1. 河南大学化学生物学研究所
- Keywords:
fluoroquinolone;
amide;
rhodanine;
unsaturated ketone;
antitumor activity;
synthesis
- From:
Journal of China Pharmaceutical University
2017;48(5):543-547
- CountryChina
- Language:Chinese
-
Abstract:
To explore a new strategy for the transformation of antibacterial activity of fluoroquinolone into antitumor activity,twelve new title compounds,1-ethyl-6-fluoro-7-(4-methyl-pipreazin-1-yl)-quinolin-4-one-3-carboxylicacid (5-arylidene-2-thioxo-1,3-thiozolidin-2,4-dione-3-yl) amides (6a-61),were designed and synthesized with an amide group and a rhodanine unsaturated ketone moiety as an isostere and modified group,respectively,from pefloxacin (1).Their structures were characterized by elemental analysis and spectral data.The in vitro antitumor activity of the title compounds against Hep-3B,Capan-1 and L1210 cell lines exhibited more significant potency than pefloxacin.The compounds with aromatic heterocyclic or flurophenyl displayed comparable activity to the comparasion doxorubicin.Thus,rhodanine unsaturated ketone hybrided amide group as an isostere of the C-3 carboxylic acid group appears to be an alternative route for further design of antitumor fluoroquinolone.
