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Cyclopentyl derivatives of 8‐azahypoxanthine and 8‐azaadenine. Carbocyclic analogs of 8‐azainosine and 8‐azaadenosine
Author(s) -
Shealy Y. Fulmer,
Clayton Joe D.,
Allen O'Dell C.
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100431
Subject(s) - chemistry , hydroxymethyl , cyclopentane , stereochemistry , hydrolysis , pyrimidine , liquid ammonia , ammonia , medicinal chemistry , organic chemistry
Four types of carboeyclic analogs of 8‐azahypoxanthine and 8‐azaadenine nucleosides have been prepared. This group of analogs is comprised of derivatives having the (±)‐ as ‐3‐(hydroxy‐methyl)cyclopentyl,(±)‐ trans ‐3‐hydroxy‐ cis ‐4‐(hydroxymethyl)cyclopentyl), (±)‐ trans ‐2‐hydroxy‐ cis ‐4‐(hydroxymethyl)cyclopentyl, and (±)‐ trans ‐2, trans ‐3‐dihydroxy‐ cis ‐4‐(hydroxymethyl)‐cyelopentyl groups at position 3 of 3,6‐dihydro‐7 H ‐ v ‐triazolo[4,5‐ d ]pyrimidm‐7‐one and of 7‐amino‐3 H ‐ v ‐triazolo[4,5‐ d ]pyrimidine. Diazotization of (5‐amino‐6‐chloropyrimidin‐4‐yl‐amino)eyclopentane derivatives and acidic hydrolysis, without isolation of the resulting 7‐chloro‐3 H ‐ v ‐triazolo[4,5‐ d ]pyrimidines yielded the 8‐azahypoxanthine derivatives (III). Treatment of unpurified 7‐chloro‐3 H ‐ v ‐triazolo[4,5‐ d ]pyrimidines with anhydrous ammonia gave the 8‐azaadenine derivatives (IV). The cyclopentane analogs of 8‐azaadenylic acid and of 8‐aza‐adenosine 3′,5′ ‐cyclic monophosphate were prepared from the 8‐azaadenosine analog.