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Citation: CHEN Yinsheng, WANG Guoqiang, DUAN Nannan, CAO Tieyao, WEN Xiaoyi, YIN Jun, WANG Wei, XIE Songqiang, HUANG Wenlong, HU Guoqiang. Synthesis and Antitumor Activity of Fluoroquinolone C3-Isostere Derivatives: Oxadiazole Mannich Base Derivatives[J]. Chinese Journal of Applied Chemistry, ;2012, 29(11): 1246-1250. doi: 10.3724/SP.J.1095.2012.00537 shu

Synthesis and Antitumor Activity of Fluoroquinolone C3-Isostere Derivatives: Oxadiazole Mannich Base 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: 30 November 2011
Available Online: 9 January 2012
Fund Project: 国家自然科学基金(20872028,21072045) (20872028,21072045)河南大学科研基金(06YBZR075)资助项目 (06YBZR075)

To further study an efficient modified route for transforming an antibacterial fluoroquinolone to an antitumor compound,an oxadiazole heterocyclic ring,1,3,4-oxadiazole-thione,was used as an isostere of C-3 carboxylic group for pefloxacin 1,and a key intermediate,1-ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-3-(3H-1,3,4-oxadiazole-2-thione-5-yl)-quinolin-4(1H)-one 4(5),was designed and synthesized.The intermediate was then subjected to an aminomethylation reaction with secondary amines or substituted anilines and formaldehyde to afford the corresponding oxadiazole thione Mannch bases 6a~6j as the title compounds,respectively.The structures for ten 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.The results reveal that all the title compounds show more significant potent than that of parent compound 1,and those derived from aliphatic amines display higher activity than the aromatic amine compounds.
- fluoroquinolone,
- isostere,
- oxadiazole thione,
- Mannich base,
- antitumor evaluation
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