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Synthesis of L-1-(2-Azido-2-deoxyribofuranosyl)cytosine as potential antiviral agent

Title
Synthesis of L-1-(2-Azido-2-deoxyribofuranosyl)cytosine as potential antiviral agent
Authors
연숙희
Issue Date
2001
Department/Major
대학원 약학과
Publisher
이화여자대학교 대학원
Degree
Master
Abstract
일반적으로 D-nucleosides의 거울상 이성질체인 L-nucleosides는 D-nucleosides보다 독성이 적은 것으로 알려져 있고, 항바이러스 활성과 항암 활성을 나타내면서 독성이 경감된 L-2'-deoxy-4'-thiopyrimidine nucleosides 유도체가 합성되었다. 또한 최근에 L-nucleosides와 4'-thionucleosides의 항암 활성과 항바이러스 활성도 보고되었다. 이러한 사실에 기인하여 새로운 L-1-(2-azido-2-deoxy-4-thioribo-furanosyl)cytosine을 합성하였다. 최종물질은 benzoic acid 2,4-bis-benzyloxy-1-(bis-benzylsulfanyl-methyl)-3-hydroxy-butyl ester을 출발물질로 하여 중요 중간체인 L-2-azido-2-deoxy-4-thioribofuranose를 거쳐 총 15 step으로 합성하였으며 전자 공여기와 전자 흡인기에 따라 핵산 염기의 축합 반응이 영향을 받는다는 것을 발견하였다.;Since L-nucleosides were in general found to be less toxic than their corresponding enantiomers, D-nucleosides, L-2'-deoxy-4'-thiopyrimidine nucleosides have been synthesized for the development of antiviral and anticancer agents. Several 2'-modified 2'-deoxy-4'-thiocytidines have been found to show potent antiviral and antitumor activities. Prompted by the impressive antiviral activity and toxicity profile displayed by L-nucleosides and 4'-thionucleosides, L-1-(2-azido-2-deoxy-4-thioribofuranosyl) cytosine was synthesized starting from D-xylose via the key intermediate, L-2-azido-2-deoxy-4-thioribofuranose as potential antiviral agent.
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일반대학원 > 생명·약학부 > Theses_Master
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