9- 氯吖啶与2- 甲氧基-4- 硝基苯胺发生芳香亲核取代反应制得3- 甲氧基-4-(9- 吖啶基氨基) 硝基苯，然后经氯化亚锡还原得3- 甲氧基-4-(9- 吖啶基氨基) 苯胺，最后经甲磺酰化反应得到抗肿瘤药安吖啶，总收率为39％。
Abstract
Amsacrine, an antitumor drug, was prepared from 9-chloroacridine via nucleophilic aromatic substitution with 2-methoxy-4-nitroaniline to give 3-methoxy-4-(9-acridinylamino)nitrobenzene, which was subjected to reduction with stannous chloride to obtain 3-methoxy-4-(9-acridinylamino)aniline, followed by methanesulfonyl reaction with an overall yield of 39％.
关键词
安吖啶 /
抗肿瘤药 /
合成 /
工艺
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Key words
amsacrine /
antitumor drug /
synthesis /
process
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参考文献
[1] Cysyk RL, Shoemaker DD, Ayers OC, et al. Oral absorption and selective tissue localization of 4'-(9-acridinylamino)- methanesulfon-m-anisidide [J]. Pharmacology, 1978, 16(4):206-213.
[2] 王建安. 安吖啶的临床应用[J]. 人民军医, 1989, 39(9):69-70.
[3] Brennan ST, Colbry NL, Leeds RL, et al. Anticancer anilinoacridines. A process synthesis of the disubstituted amsacrine analog CI-921 [J]. J Heterocycl Chem, 1989,26(5): 1469-1476.
[4] Ferlin MG, Marzano C, Chiarelotto G, et al. Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives [J]. Eur J Med Chem,2000, 35(9): 827-837.
[5] Atwell GJ, Rewcastle GW, Baguley BC, et al. Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity [J]. J Med Chem, 1987, 30(4): 652-658.
[6] Kunikowski A. Preparation of 4-( acridinylamino) -3- methoxymethane sulfonanilide: PL, 149149B1 [ P] .
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脚注
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基金
国家自然科学基金项目(21272056)、河南省教育厅项目(2010B350002)
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