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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (02): 404-408 .DOI: 10.6023/cjoc1105252 上一篇    下一篇

研究简报

1-羟基异喹啉及羟基Fasudil 的合成

陈美珠a, 刘帅a, 王欣然a, 罗浩a, 陈立功a, 王东华b   

  1. a 天津大学化工学院精细化工系 天津 300072;
    b 天津大学药物科学与技术学院 天津 300072
  • 收稿日期:2011-05-25 修回日期:2011-08-29 发布日期:2012-03-09
  • 通讯作者: 王东华 E-mail:wdh022@tju.edu.cn

Synthesis of 1-Isoquinolinol and Hydroxyfasudil

Chen Meizhua, Liu Shuaia, Wang Xinrana, Luo Haoa, Chen Ligonga, Wang Donghuab   

  1. a Institute of Chemical Engineering and Technology, Tianjin University, Tianjin 300072;
    b School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072
  • Received:2011-05-25 Revised:2011-08-29 Published:2012-03-09

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被引次数

10 | 3

首先以异喹啉为原料, 经氧化生成氮氧化物后与苯甲酰氯和水作用, 得到1-羟基异喹啉, 收率为73.3%. 以Fasudil 为原料, 经氨基保护、氧化, 在相转移催化剂的存在下, 于二氯甲烷和水的两相体系中与苯甲酰氯和水作用, 合成羟基Fasudil, HPLC 纯度大于99%, 总收率为46.8%, 从而建立了一条条件温和、操作简便的羟基Fasudil 的合成工艺路线.

关键词: 1-羟基异喹啉, 氮氧化物, Fasudil, 羟基Fasudil

1-Isoquinolinol was synthesized from isoquinoline via oxidation, reaction with benzoyl chloride and water in yield of 73.3%. According to this process, a method for the synthesis of hydroxyfasudil [1-(1-hydroxy-5-isoquinolinesulfonyl)- homopiperazine] from fasudil [hexahydro-1-(5-isoquinoline-sulfonyl)-1H-1,4-diazepine] was estabilshed in this paper. The process undergoes effectively through protection for amino, oxidation, reaction with water in a water/dichloromethane biphase system in the presence of phase transfer catalyst and benzoyl chloride and then deprotection. The objective product was finally obtained in yield of 46.8% with a purity more than 99% (HPLC). It is virtually a practical process with mild reaction conditions and simple operation.

Key words: 1-isoquinolinol, nitrogen oxide, fasudil, hydroxyfasudil