引用本文:
陈寅生, 王国强, 段楠楠, 曹铁耀, 温晓漪, 银俊, 王伟, 谢松强, 黄文龙, 胡国强. 抗肿瘤氟喹诺酮C3等排衍生物——二唑曼尼希碱衍生物的合成和抗肿瘤活性[J]. 应用化学,
2012, 29(11): 1246-1250.
doi:
10.3724/SP.J.1095.2012.00537
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
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
抗肿瘤氟喹诺酮C3等排衍生物——二唑曼尼希碱衍生物的合成和抗肿瘤活性
English
Synthesis and Antitumor Activity of Fluoroquinolone C3-Isostere Derivatives: Oxadiazole Mannich Base Derivatives
Abstract:
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.
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Key words:
- fluoroquinolone
- / isostere
- / oxadiazole thione
- / Mannich base
- / antitumor evaluation
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