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Citation: WANG Guoqiang, DUAN Nannan, CAO Tieyao, WEN Xiaoyi, YIN Jun, WANG Wei, XIE Songqiang, HUANG Wenlong, HU Guoqiang. Antitumor Fluoroquinolone C3-Isostere Derivatives(Ⅰ)——Synthesis and Activity of Bis-oxadiazole Methyl-sulfide Derivatives[J]. Chinese Journal of Applied Chemistry, ;2012, 29(7): 769-774. doi: 10.3724/SP.J.1095.2012.00360 shu

Antitumor Fluoroquinolone C3-Isostere Derivatives(Ⅰ)——Synthesis and Activity of Bis-oxadiazole Methyl-sulfide Derivatives

1.
a Institute of Chemistry & Biology, Henan University, Kaifeng 475001, China;
2.
b Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China

Corresponding author: HU Guoqiang,
Received Date: 17 August 2011
Available Online: 9 November 2011
Fund Project: 国家自然科学基金(20872028,21072045) (20872028,21072045)河南大学科研基金(06YB2R075)资助项目 (06YB2R075)

To discover an efficient modification for shifting from an antibacterial fluoroquinolone to an antitumor one based on the topological similarities between targeting topoisomerases as the eukaryotic ones and mammals,using oxadiazole heterocycle as an intermediate for the isostere of C-3 carboxylic group of norfloxacin(1),1-ethyl-6-fluoro-7-piperazin-1-yl-3-(5-mercapto-1,3,4-oxadiazol-2-yl)-quinolin-4(1H)-one(3) was subjected to thioetherfication with each of chloromethyl oxadiazole(4a~4e) to give bis-oxadiazole methylsulfides(5a~5e),respectively.The following N-methylations and quaternizations yielded the corresponding N-methyl bis-oxadiazole methylsulfides(6a~6e) and N,N-dimethyl bis-oxadiazole methylsulfide iodides(7a~7e).The structures of fifteen title compounds were characterized by elemental analysis,¹H NMR and MS,and their anticancer activities in vitro against Hep-3B cancer cell lines were also evaluated with a MTT assay.The results reveal that fifteen title compounds show higher cytotoxicity than that of comparison 1,in which quaternary ammonium salts exhibit potential anticancer activity with IC₅₀ values below 25.0 μmol/L.
- fluoroquinolone,
- isostere,
- oxadiazole,
- quaternary ammonium salt,
- antitumor evaluation
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