First synthesis and anti-HIV evaluation of 4'-methyl-cyclopentanyl 9-deazaadenosine.
The first synthesis of a 4'-methylated carbocyclic C-nucleoside 16 was achieved via the mesylate intermediate 10, which was prepared using ring-closing metathesis and S(N)2 alkylation from acetol 5. When antiviral evaluation of synthesized compound 16 was performed against various viruses such as HIV, HSV-1, HSV-2, and HCMV, it showed moderate anti-HIV activity in MT-4 cell line (EC(50) = 14.7 micromol).
Oh
Chang Hyun
CH
Medicinal Chemistry Research Center, Korea Institute of Science and Technology, Seoul, Republic of Korea.
Liu
Lian Jin
LJ
Hong
Joon Hee
JH
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D003587:Cytomegalovirus / Q000187:drug effects; D006678:HIV / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure
C532642:4'-methylcyclopentanyl 9-deazaadenosine; D019380:Anti-HIV Agents; D008698:Mesylates; D000241:Adenosine