Synthesis of cyclobutane analogues of the antiviral cyclopropane nucleoside A-5021.
Cyclobutane analogues of the antiviral cyclopropane nucleoside A-5021 were synthesized from 1-cyano-1,2-bis(methoxycarbonyl)cyclobutane via 1) isolation of both diastereomers by crystallization, 2) reduction to aminodiol, 3) coupling with 2-amino-4,6-dichloropyrimidine, and 4) guanine ring formation. Despite their structural resemblance to A-5021, the compounds were devoid of antiherpetic activity.
Onishi
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T
Pharmaceutical Research Laboratories, Ajinomoto Co. Inc., Kawasaki, Japan.
Tsuji
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T
D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D001671:Biochemistry / Q000379:methods; D003503:Cyclobutanes / Q000737:chemistry*; D006147:Guanine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology*; D018259:Herpesvirus 1, Human / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
C111645:9-((cis-1,2-bis(hydroxymethyl)cycloprop-1-yl)methyl)guanine; D000998:Antiviral Agents; D003503:Cyclobutanes; D006147:Guanine