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2-甲基-1-取代-咪唑并[4,5-g]喹啉-4,9-二酮和7,8-二氢-10H-[1,4]恶嗪并[3',4':2,3]咪唑并[4,5-g]喹啉-5,12-二酮衍生物的合成与细胞毒性

Synthesis and cytotoxicity of 2-methyl-1-substituted-imidazo [4,5-g]quinoline-4,9-dione and 7,8-dihydro-10H-[1,4]oxazino[3',4':2,3]imidazo[4,5-g]quinoline-5,12-dio ne derivatives.

作者信息

Suh M E, Kang M J, Yoo H W, Park S Y, Lee C O

机构信息

Division of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, South Korea.

出版信息

Bioorg Med Chem. 2000 Aug;8(8):2079-83. doi: 10.1016/s0968-0896(00)00132-2.

DOI:10.1016/s0968-0896(00)00132-2
PMID:11003153
Abstract

2-Methyl-1-substituted-imidazo[4,5-g]quinoline-4,9-diones and 7,8-dihydro-10H-[1,4]oxazino-[3',4':2,3]imidazo[4,5-g]quinoline-5, 12-dione (19) derivatives have been synthesized from 6,7-dichloro-5,8-quinolinedione for developing the new anticancer drugs. Our study on the cytotoxicity of imidazoquinolinedione derivatives has revealed that 7,8-dihydro-10H-[1,4]oxazino-[3',4':2,3]imidazo[4,5-g]quinoline-5, 12-dione (19), a tetracyclic heteroquinone analogue, exhibited high cytotoxicity on human colon tumor cell (HCT 15) in vitro SRB assay. The IC50 value of this compound was 0.026 microg/mL whereas those of doxorubicin and cisplatin were 0.023 microg/mL and 1.482 microg/mL, respectively. Meanwhile compounds 5-7 and 12 in the series of 1-substituted-imidazoquinolinediones showed relatively good activity on human brain tumor cell lines (XF 498).

摘要

为研发新型抗癌药物，已从6,7-二氯-5,8-喹啉二酮合成了2-甲基-1-取代-咪唑并[4,5-g]喹啉-4,9-二酮和7,8-二氢-10H-[1,4]恶嗪并-[3',4':2,3]咪唑并[4,5-g]喹啉-5,12-二酮（19）衍生物。我们对咪唑并喹啉二酮衍生物细胞毒性的研究表明，四环杂醌类似物7,8-二氢-10H-[1,4]恶嗪并-[3',4':2,3]咪唑并[4,5-g]喹啉-5,12-二酮（19）在体外SRB试验中对人结肠肿瘤细胞（HCT 15）表现出高细胞毒性。该化合物的IC50值为0.026μg/mL，而阿霉素和顺铂的IC50值分别为0.023μg/mL和1.482μg/mL。同时，1-取代-咪唑并喹啉二酮系列中的化合物5-7和12对人脑肿瘤细胞系（XF 498）显示出相对较好的活性。

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