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Mesoionic isoxazolo[2,3‐ a ]pyrimidinediones and 1,3,4‐oxadiazolo[3,2‐ a ]pyrimidinediones as potential adenosine antagonists
Author(s) -
Shehata Ihsan A.,
Glen Richard A.
Publication year - 1987
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.5570240511
Subject(s) - mesoionic , chemistry , ring (chemistry) , stereochemistry , adenosine , position (finance) , purine , medicinal chemistry , organic chemistry , enzyme , biochemistry , finance , economics
Abstract Several derivatives of two novel mesoionic ring systems, i.e. , isoxazolo[2,3‐ a ]pyrimidinedione and 1,3,4‐oxadiazolo[3,2‐ a ]pyrimidinedione, were prepared for evaluation as adenosine antagonists. Whereas both ring systems are relatively stable when the 6‐position ( i.e. , that position corresponding to the purine 1‐position) is substituted by an alkyl group, neither ring system is stable when this position is unsubstituted. An example of a 6‐unsubstituted non‐mesoionic isoxazolopyrimidinedione exhibited similar behavior. As adenosine antagonists, the mesoionic compounds were found to be less potent than their previously evaluated mesoionic thiadiazolo[3,2‐ a ]pyrimidinedione counterparts.