Synthesis and antiviral activity of novel C-methyl branched cyclopropyl nucleosides.
A series of novel cyclopropyl nucleosides was synthesized using the highly stereoselective Simmons-Smith reaction starting from 1,2:5,6-di-O-isopropylidene-D-mannitol. The structural assignments of these nucleosides were determined by NMR studies and X-ray crystallography. All the synthesized nucleosides were assayed against several viruses.
Kwak
Eun Yee
EY
College of Pharmacy, Chonnam National University, Kwangju 500-757, Korea.
Hong
Joon Hee
JH
Park
Youngja
Y
Choi
Bo Gil
BG
D000225:Adenine / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000494:pharmacology; D003587:Cytomegalovirus / Q000187:drug effects; D003601:Cytotoxicity Tests, Immunologic; D015774:Ganciclovir / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D007723:Korea; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011687:Purines / Q000138:chemical synthesis / Q000494:pharmacology; D012254:Ribavirin / Q000494:pharmacology; D015215:Zidovudine / Q000494:pharmacology
C487392:(1'S,2'S)-2-amino-9-((2'-hydroxyethyl-1'-(methyl)cycloprop-1'-yl)methyl)-6-chloropurine; C487391:(1'S,2'S)-9-((2'-hydroxymethyl-1'-(methyl)cycloprop-1'-yl)methyl)adenine; D000998:Antiviral Agents; D003521:Cyclopropanes; D011684:Purine Nucleosides; D011687:Purines; D012254:Ribavirin; D015215:Zidovudine; D000225:Adenine; D015774:Ganciclovir