Studies on the Synthesis of Etodolac Derivatives as Potential Anti-inflammatory Agents

항염증제인 Etodolac 유도체의 합성에 관한 연구

  • Cho, Hoon (Department of Chemistry, Chungbuk National University) ;
  • Chung, Yong Seog (Department of Chemistry, Chungbuk National University) ;
  • Jang, Hang Dong (Department of Chemical Engineering, Seoul National Polytechnic University) ;
  • Ryu, Seong Ryual (Department of Chemical Engineering, Dae Bul University)
  • 조훈 (충북대학교 화학과) ;
  • 정용석 (충북대학교 화학과) ;
  • 장향동 (서울산업대학교 화학공학과) ;
  • 류성렬 (대불대학교 화학공학과)
  • Received : 1998.08.24
  • Accepted : 1998.09.25
  • Published : 1999.02.10


For the synthesis of new anti-inflammatory agents as indol derivatives, we have synthesized ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester. It was a new method for ${\alpha}$-substituted etodolac carboxylic acid. The synthetic process was composed of four steps, and 7-ethylindole and oxalyl chloride were used as starting materials. The third step, cyclization was carried out by addition of borontrifluoride diethyl etherate in 66% yield. The step of reduction and cyclization were simplified successfully. The final product, ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester was obtained in 66% yield by the reaction of methyl 1,8-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate (etodollic acid methyl ester) and benzoyl chloride.


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