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Synthesis of 3′-Azido-2′, 3′-dideoxy-4′-selenouridine As Potential Anti-HIV Agent

Title
Synthesis of 3′-Azido-2′, 3′-dideoxy-4′-selenouridine As Potential Anti-HIV Agent
Other Titles
3′-azido-2′, 3′-dideoxy-4′-selenouridine 의 잠재적인 항 HIV 약물로서의 합성
Authors
전정하
Issue Date
2010
Department/Major
대학원 생명·약학부약학전공
Publisher
이화여자대학교 대학원
Degree
Master
Advisors
정낙신
Abstract
HIV-1 RT (human immunodeficiency virus type 1 reverse transcriptase) has become the most attractive target to develop new anti-HIV drugs. Unfortunately, drug resistance still occur despite of good activity of AZT and AZDU. To discover new templates for anti-HIV agents, we have reported the stereoselective synthesis of 3'-azido-2',3'-dideoxy-4'-selenouridine as a novel anti-HIV agent. The synthesis of the 3'-Azido-2',3'-dideoxy-4'-selenouridine (4) was accomplished from D-2-deoxy-ribose. The key steps of the synthetic pathway are the conversion of 5 position hydroxyl group of 8 via Mitsunobu reaction, condensation of selenosugar 6 with uracil and debenzylation of 17. All elements for each reaction were optimized with great efforts. Anti-HIV assay of the synthesized 4'-seleno-AZDU (4) is in progress and will be reported elsewhere.;새로운 항HIV 약물을 개발에서 HIV-1 RT (human immunodeficiency virus type 1 reverse transcriptase)은 가장 선호되는 target이다. 안타깝게도 현재 개발되어있는AZT와 AZDU의 좋은 활성에도 불구하고 약물저항성을 가지는 HIV 바이러스 변종이 끊임없이 나타 나고 있으며, 이러한 바이러스 변종을 치료하기 위하여 3′-azido-2′,3′-dideoxy-4′-selenouridine (4) 이 입체선택적으로 합성되었다. 3′-Azido-2′,3′-dideoxy-4′-selenouridine (4) 은 D-2-deoxy-ribose로부터 합성되었으며 8번 물질의 5번 위치 수산기의 Mitsunobu 반응을 통한 입체전환과 selenosugar 6 과 uracil의 축합반응, 17번 물질의 debenzylation 반응이 합성과정에서 중요한 반응으로 보고되었다. 합성된 4′-seleno-AZDU (4) 가 anti-HIV 활성을 나타낼 것으로 기대한다.
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