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제126회 대한화학회 학술발표회 및 총회 Design, Synthesis, and Anti-RNA Virus Activity of 6′-Fluorinated-Aristeromycin Analogues

등록일
2020년 9월 10일 17시 24분 36초
접수번호
1040
발표코드
ORGN1-4 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
화 11시 : 55분
발표형식
심포지엄
발표분야
Organic Chemistry - Current Trends in Organic Chemistry I: Medicinal Chemistry & Chemical Biology
저자 및
공동저자
Gyudong Kim, Lak Shin Jeong1,*
College of Pharmacy, Chonnam National University, Korea
1Department of Pharmacy, Seoul National University, Korea
(−)-Aristeromycin, isolated from Streptomyces citricolor, is a representative carbocyclic nucleoside that exists in nature. This compound is a potent inhibitor of S-adenosylhomocysteine (AdoHcy) hydrolase and shows potent antiviral activities against several RNA and DNA viruses. Based on this natural product, (−)-6′-β-fluoro-aristeromycin has been synthesized via stereoselective electrophilic fluorination followed by a purine base build-up approach. And the 6′-fluorinated aristeromycin analogues were designed as dual-target antiviral compounds aimed at inhibiting both the viral RNA-dependent RNA polymerase (RdRp) and the host cell S-adenosyl-L-homocysteine (SAH) hydrolase, which would indirectly target capping of viral RNA. The introduction of a fluorine at the 6′-position enhanced the inhibition of SAH hydrolase and the activity against RNA viruses. References 1. Yoon, J-S.†; Kim, G.†; Jarhad, D. B.; Kim, H-R.; Shin, Y-S.; Qu, S.; Sahu, P. K.; Kim, H. O.; Lee, H. W.; Wang, S. B.; Kong, Y. J.; Chang, T-S.; Ogando, N. S.; Kovacikova, K.; Snijder, E. J.; Posthuma, C. C.; van Hemert, M. J.; Jeong, L. S. “Design, Synthesis, and Anti-RNA Virus Activity of 6′-Fluorinated-Aristeromycin Analogues” J. Med. Chem. 2019, 62, 6346-6362. (†1st co-author) 2. Kim, G.; Yoon, J.-S.; Jarhad, D. B.; Shin, Y. S.; Majik, M. S.; Mulammutti, V. A.; Hou, X.; Qu, S.; Park, J.; Baik, M.-H.; Jeong, L. S. “Asymmetric Synthesis of (-)-6'-b-Fluoro-aristeromycin via Stereoselective Electrophilic Fluorination” Org. Lett. 2017, 19, 5732-5735.

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