期刊
JOURNAL OF MEDICINAL CHEMISTRY
卷 49, 期 3, 页码 1140-1148出版社
AMER CHEMICAL SOC
DOI: 10.1021/jm0509750
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资金
- NIAID NIH HHS [N01 AI 30049, N01 AI 30048, U019 AI 056540] Funding Source: Medline
A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by the ring-closing metathesis (RCM) reaction with Grubbs catalysts provided (+)-12a on a 10 g scale with 52% overall yield from D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC50 0.4 mu M) against vaccinia virus and moderate activities (EC50 39 mu M) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC50 47 mu M). The 1,2,4-triazole analogue (17a) also exhibited moderate antiviral activity (EC50 21 mu M) against SARSCoV.
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