Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

Chemical Research in Chinese Universities ›› 2012, Vol. 28 ›› Issue (6): 980-984.

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Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

HU Guo-qiang¹, WANG Guo-qiang¹, DUAN Nan-nan¹, WEN Xiao-yi¹, CAO Tie-yao¹, XIE Song-qiang¹, HUANG Wen-long²

1. Institute of Pharmacy, Henan University, Kaifeng 475001, P. R. China;
2. Centre of Drug Discovery, China Pharmaceutical University, Nanjing 210009, P. R. China

Received:2012-02-20 Revised:2012-04-17 Online:2012-11-25 Published:2012-11-09
Contact: HU Guo-qiang E-mail:hgqxy@sina.com.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20872028, 21072045).

Abstract

Abstract:

To discover an efficient route for the shift from an antibacterial fluoroquinolone to an antitumor one based on the mechanistic similarities between targeting topoisomerases and the eukaryotic ones, two series of the title compounds, C3 bis-oxadiazole methylsulfides 6a-6h and corresponding dimethylpiperazinium iodides 7a-7h derived from levofloxacin 1 were designed and synthesized. Their in vitro antiproliferative activities against Chinese hamster ovary cell line(CHO), murine leukemia cell line(L1210) and human leukocytoma cell line(HL60) were evaluated by MTT assay, and inhibitory effect on DNA topoisomerase IIα was also measured by means of densitometric assay.

Key words: Fluoroquinolone, Oxadiazole, Isostere, Sulfide, Piperazinium, Antitumor activity

HU Guo-qiang, WANG Guo-qiang, DUAN Nan-nan, WEN Xiao-yi, CAO Tie-yao, XIE Song-qiang, HUANG Wen-long. Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin[J]. Chemical Research in Chinese Universities, 2012, 28(6): 980-984.

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Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

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