YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of Fluorinated New Thebaine Derivatives

불소기가 치환된 새로운 티베인 유도체 합성 -진통작용 검색 및 친화력 검토를 중심으로

  • Kim, Keun-Jae (Department of Applied Chemistry, Han Nam University) ;
  • Kim, Su-Man (Department of Applied Chemistry, Han Nam University)
  • Published : 1998.06.01
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Abstract

5-Methylthebaine was obtained by treating thebaine with n-butyllithium and methylfluorosulfonate. Hetero Diels-Alder reaction of thebaine and 5-methylthebaine with trifluoroacet aldehyde afforded 14-${\beta}$-(triflu-oro-2-hydroxyethyl)codeine (2) and 14-${\beta}$-(trifluoro-2-hydroxyethyl)-5-methylcodeinone (9). 6-${\alpha}$-OH compound (4) was obtained by employing $CeCl_2$ and $NaBH_4$. After synthesized a derivative substituted for 3-OH (5), using boron tribromied, We synthesized a new derivative that make double bond in C-7, C-8 into epoxode (6), (10). Through inspecting an influence on structure-activity and analgetic action, we are going to examine which opiold acceptor has a selectivity.

Keywords

References

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