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Synthesis of homovanillic amide derivatives and their analgesic activity

Lim, Hee-Jong   (Korea Research Institute of Chemical TechnologyCC0186998  ); Jung, Young-Sik   (Korea Research Institute of Chemical TechnologyCC0186998  ); Ha, Deok-Chan   (Korea Research Institute of Chemical TechnologyCC0186998  ); Seong, Churl-Min   (Korea Research Institute of Chemical TechnologyCC0186998  ); Lee, Jong-Cheol   (Korea Research Institute of Chemical TechnologyCC0186998  ); Choi, Jin-Il   (Korea Research Institute of Chemical TechnologyCC0186998  ); Choi, Seung-Won   (Korea Research Institute of Chemical TechnologyCC0186998  ); Han, Man-So   (Korea Research Institute of Chemical TechnologyCC0186998  ); Lee, Kwang-Sook   (Korea Research Institute of Chemical TechnologyCC0186998  ); Park, No-Sang   (Korea Research Institute of Chemical TechnologyCC0186998  );
  • 초록

    In the previous reports (Park et al., 1991, and 1993), we described the synthesis and analgesic effects of various homovanillic amides as analogs of capsaicin. In the study, we tried to enhance the analgesic actvity of capsaicin by structural modification. Our study has been performed in three directions. First, the amide bond of capsaicin was transposed. Second, a phenyl ring was introduced to replace a double bond of capsaicin. Finally, aminoethylation was performed on 4-hydroxy group of capsaicin to improve oral bioavailability. These studies have led to N-(3-phenylpropyl)homovanillic amide 2 which has high analgesic activity. Our continuing efforts in this area have focused on the introduction of various substituents on the phenyl ring of 2 as well as their pharmacological studies. We report herein the synthesis of homovanillic amide derivatives and their analgesic activity.


  • 주제어

    capsaicin .   analgesic activity .   structure-activity .   re-lationship.  

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