Synthesis and antitumor activity of pefloxacin C-3 methylene rhodanine devatives
10.11665/j.issn.1000-5048.20190606
- VernacularTitle:培氟沙星C-3甲叉基绕丹宁衍生物的合成及其抗肿瘤活性
- Author:
Huili ZHANG
1
;
Guangli LU
;
Wenlong HUANG
;
Guoqiang HU
Author Information
1. 郑州工业应用技术学院药学院
- Publication Type:Journal Article
- Keywords:
pefloxacin;
fluoroquinolone-3-carbaldehyde;
rhodanine;
unsaturated ketone;
bioisostere;
antitumor activity
- From:
Journal of China Pharmaceutical University
2019;50(6):672-677
- CountryChina
- Language:Chinese
-
Abstract:
To further explore an efficient strategy for the construction of antitumor fluoroquinolone molecules from antibacterial fluoroquinolone drugs, twelve new title compounds, 1-ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-3-(3-substituted-rhodanin-5-ylidene)methyl-quinolon-4(1H)-ones(6a-6l), was designed and synthesized with α, β-unsaturated ketone scaffold and a rhodanine ring as an isostere and fused modified group, respectively, from pefloxacin(1), and their structures were characterized by elemental analysis and spectral data. The in vitro anti-cell proliferative activity of the title compounds against the tested A549, Hep-3B and HL60 cancer cells exhibited more significant potency than parent 1. In particular, halogenated phenyl title compounds(6d, 6e, 6f)displayed a comparable activity to comparison doxorubicin against A549 cells and low cytotoxicity against normal Vero cells. Thus, a methylene rhodanine scaffold as a bioisostere of the C-3 carboxylic acid group have shown to be beneficial to improving the antitumor activity.
