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高等学校化学研究 ›› 2011, Vol. 27 ›› Issue (1): 66-69.

• Articles • 上一篇    下一篇

Novel Method for Synthesis of Diarylpyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists

WU Ying-qiu1, ZHENG Guo-jun2, WANG Ya-ping2, WANG Xiang-jing1 and XIANG Wen-sheng1*   

  1. 1. Department of Biochemical Engineering, Northeast Agricultural University, Harbin 150030, P. R. China;
    2. Zhejiang Hisun Pharmaceutical Co., Ltd., Taizhou 318000, P. R. China
  • 收稿日期:2010-02-03 修回日期:2010-04-21 出版日期:2011-01-25 发布日期:2011-01-04
  • 通讯作者: XIANG Wen-sheng E-mail:xiangwensheng@yahoo.com.cn
  • 基金资助:

    Supported by the Program for New Century Excellent Talents in University of China(Nos.NCET-08-0668, 1154-NCET-002) and the Outstanding Youth Foundation of Heilongjiang Province, China(No.JC200706).

Novel Method for Synthesis of Diarylpyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists

WU Ying-qiu1, ZHENG Guo-jun2, WANG Ya-ping2, WANG Xiang-jing1 and XIANG Wen-sheng1*   

  1. 1. Department of Biochemical Engineering, Northeast Agricultural University, Harbin 150030, P. R. China;
    2. Zhejiang Hisun Pharmaceutical Co., Ltd., Taizhou 318000, P. R. China
  • Received:2010-02-03 Revised:2010-04-21 Online:2011-01-25 Published:2011-01-04
  • Contact: XIANG Wen-sheng E-mail:xiangwensheng@yahoo.com.cn
  • Supported by:

    Supported by the Program for New Century Excellent Talents in University of China(Nos.NCET-08-0668, 1154-NCET-002) and the Outstanding Youth Foundation of Heilongjiang Province, China(No.JC200706).

PDF (PC)

摘要： A novel and efficient method was developed for the synthesis of diarylpyrazole derivatives as cannabinoid CB1 receptor antagonist via four step reactions. The key step was the synthesis of a diarylpyrazole skeleton, which involved initial condensation of the sodium salt of compound 12 with diazonium compounds, and further cyclization by heating at reflux in acetic acid. Eight diarylpyrazole derivatives and nine new synthesized compounds were characterized by 1H NMR, IR, MS, and elemental analysis. The reaction conditions were mild and the overall yields of the target compounds ranged from 26% to 44%.

关键词: Cannabinoid CB1 receptor antagonist, Diarylpyrazole derivative, SR141716

Abstract: A novel and efficient method was developed for the synthesis of diarylpyrazole derivatives as cannabinoid CB1 receptor antagonist via four step reactions. The key step was the synthesis of a diarylpyrazole skeleton, which involved initial condensation of the sodium salt of compound 12 with diazonium compounds, and further cyclization by heating at reflux in acetic acid. Eight diarylpyrazole derivatives and nine new synthesized compounds were characterized by 1H NMR, IR, MS, and elemental analysis. The reaction conditions were mild and the overall yields of the target compounds ranged from 26% to 44%.

Key words: Cannabinoid CB1 receptor antagonist, Diarylpyrazole derivative, SR141716