서지주요정보
Synthesis and biological activity of opioid analgesics = 오피오이드 진통제의 합성 및 생체활성
서명 / 저자 Synthesis and biological activity of opioid analgesics = 오피오이드 진통제의 합성 및 생체활성 ; Deoxygenation of alcohols with tetrabutylammonium peroxydisulfate and formate ion = 테트라부틸암모늄 퍼옥시다이설페이트와 포름산염을 이용하는 알코올의 탈산소화반응 / Hee-Sock Park.
저자명 Park, Hee-Sock ; 박희석
발행사항 [대전 : 한국과학기술원, 2006].
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8016928

소장위치/청구기호

학술문화관(문화관) 보존서고

DCH 06002

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초록정보

A variety of buprenorphine analogs have been synthesized. In the studies of analgesic and addictive effects in mice and $[^{35}S]GTP\gammaS$ binding assay in human brain tissue, the new compound 16 has been identified as a selective κ partial agonist which gives antinociceptive effects, but is not self-administered. It is reported that the activation of κ receptors leads to the suppression of unpleasant μ- and δ-mediated side effects such as the rewarding effect. The fact that this compound has a profile (κ partial agonist) may lead to lower degrees of dysphoria than full κ agonists. The compound may be valuable for the development of long-lasting analgesic, as a requirement for protracted use in neuropathic pain and drug abuse medication. In addition, a new method for the efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with $(Bu_4N)_2S_2O_8$ and $HCO_2Na$ in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl derivatives from $CO_2^{\bullet -}$ rather than from $SO_4^{\bullet -}$. This type of reduction is especially important in many areas of natural product chemistry such as sugars, glycosides, and nucleosides since a selective deoxygenation of the hindered hydroxy-groups is often required in order to enhance their biological activities. Of particular note, in the case of 27c (phenyl thionocarbonate) the $(Bu_4N)_2S_2O_8/DCO_2Na$ deoxygenation system in DMSO can provide the deuterated furanose derivatives at C3 position.

서지기타정보

서지기타정보
청구기호 {DCH 06002
형태사항 v, 131 p. : 삽도 ; 26 cm
언어 영어
일반주기 부록 수록
저자명의 한글표기 : 박희석
지도교수의 영문표기 : Hee-Yoon Lee
공동교수의 영문표기 : Yong-Hae Kim
지도교수의 한글표기 : 이희윤
공동교수의 한글표기 : 김용해
수록잡지명 : "Facile barton-mccombie deoxygenation of alcohols with tetrabutylammonium peroxydisulfate and formate Ion". Organic letters, v.7 no.15 , pp. 3187-3190(2005)
수록잡지명 : "A highly selective kappa-opiod receptor agonist with low addictive potential and dependence liability". Bioorganic & medicinal chemistry letters, submitted,
학위논문 학위논문(박사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 94-100
주제 Opioid, analgesic
deoxygenation
tetrabutylammonium peroxydisulfate
formate ion
오피오이드, 진통제
탈산소화
테트라부틸암모늄 퍼옥시다이설페이트
포름산염
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