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학술발표회초록보기

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  • 09월 11일 00시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Practical Synthesis and Biological Evaluation of Carbocyclic Nucleoside Analogs

등록일
2019년 8월 27일 10시 34분 47초
접수번호
1632
발표코드
MEDI-1 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
목 15시 : 40분
발표형식
심포지엄
발표분야
Medicinal Chemistry - Innovative Therapeutics and Diagnostic Agents in Medicinal Chemistry
저자 및
공동저자
Jong Hyun Cho
Medicinal Biotechnology, Dong-A University, Korea

A practically synthetic method for chiral cyclopentenol derivatives (Ia-b) was developed as the key intermediate that was utilized for the synthesis of biologically active carocyclic nucleosides, From D-ribose, the selective protection of allylic hydroxyl group followed by the ring closing metathesis (RCM) reaction with Grubbs’ catalyst II provided a single cyclopentanol (Ia) in 48-52% yield. The key intermediate was applied for the synthesis of unnatural five-membered ring heterocyclic carocyclic nucleosides as the neplanocin A (NPA). The novel structure, 1,2,3-triazolenucleoside (II), exhibited potent antiviral activity (EC50 0.4 μM) against vaccinia virus. In addition, the chiral cyclopentenol derivative (Ib) was used to develop an efficient synthetic route for biologically relevant (-)-5-fluorocarbodine (III), which is a potent anti-cancer agent. Direct coupling of N6-protected 5-fluorouracil with the cyclopentenol (1b), followed by formation of a macrocycle between the base and sugar moiety, via RCM reaction, allowed for a facial selective hydrogenation of the sugar double bond to give, exclusively, the desired 4’-β-stereoisomer (III).


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