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有机化学 ›› 1990, Vol. 10 ›› Issue (6): 513-516. 上一篇    下一篇

研究论文

N'羟烷基-5-氟尿嘧啶和α-5-氟尿嘧啶-N-二羧酸的研究

卓仁禧;范昌烈;廖俊;宋绮   

  1. 武汉大学化学系
  • 发布日期:1990-12-25

Study on N'hydroxyalkyl l-5-fluorouracils and α -5-fluorouracil-N'dicarboxylic acids

ZHUO RENXI;FAN CHANGLIE;LIAO JUN;SONG QI   

  • Published:1990-12-25

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5-氟尿嘧啶是一种广谱性的抗肿瘤药物, 其缺点是脂溶性小, 毒副作用较大, 为此, 对该化合物进行了大量的化学修饰工作, 本文通过2,4,-双三甲硅基-5-氟尿嘧啶分别与乙酸-W-溴代烷基酯和α-溴代丙二酸二乙酯的反应, 然后醇解, 制备了五种N'羟烷基-5-氟尿嘧啶-(2a-e)和α-5-氟尿嘧啶-N'-丙二酸二乙酯(3), 通过5-氟尿嘧啶与衣康酸二甲酯反应, 制备了α-5-氟脲嘧啶-N'-甲基丁二酸二甲酯(4)。将以上所得到的两种α-5-氟尿嘧啶-N'-二羧酸酯水解, 制得α-5-氟尿嘧啶-N'-丙二酸(5)和α-5-氟尿嘧啶-N'-甲基丁二酸(6)。

关键词: 氟脲嘧啶, 溴化合物, 丙二酸 P, 氟脲嘧啶, 酯, 核磁共振谱法, 红外分光光度法, 丁二酸 P, 乙酸 P, 丙二酸 P

N1-Hydroxyalkyl-5-fluorouracils, di-Et a-5-fluorouracil-N1-malonate, di-Me a-5 fluorouracil-N1-methylsuccinate, a-5-fluorouracil-N1-malonic acid and a-5-fluorouracil-N1-methylsuccinic acid were synthesized and structurally confirmed by 1H NMR, IR, UV and elemental anal. The antitumor activity of five 5-fluorouracil derivatives were tested against Ehrlich ascites carcinoma in mice and compared with that of 5-fluorouracil-N1-acetic acid and 5-fluorouracil-N1-propanoic acid. 5-Fluorouracil-N1-substituted dicarboxylic acids exhibited no antitumor activity. N1-Hydroxyethyl-5-fluorouracil and N1-hydroxypropyl-5-fluorouracil, with lower toxicity than 5-fluorouracil, showed an inhibition ratio of 52.40% and 67.32%, resp.

Key words: FLUOROURACILUM, FLUOROURACILUM, ESTERS, BROMINE COMPOUNDS, MALONIC ACID P, NMR SPECTROMETRY, ACETIC ACID P, INFRARED SPECTROPHOTOMETRY, BUTANEDIOIC ACID P, MALONIC ACID P

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