Studies on Xanthine Derivatives. II. : Synthesis of 1,2,3,7-Tetrahydro-6H-purin-6-ones from Xanthine Hydrolyzates

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Intramolecular cyclization of caffeidine homologues (2a and 2b) in the presence of ethanolic hydrogen chloride gave 9-oxo-1H-pyrrolo[1,2-α]purine (4a) and 11-oxo-1H-azepino[1,2-α]purine (4b) derivatives, both containing a 1,2,3,7-tetrahydro-6H-purin-6-one ring system. Purine ring system compounds, 2-monosubstituted (7) and 2,2,-disubstituted (8) 1,2,3,7-tetrahydro-6H-purin-6-ones, were synthesized by intermolecular cyclization between caffeidine and aldehydes (5) or ketones (6) in the presence of acid catalysts. Pyrolysis of 4,7,8,9,9a, 11-hexahydro-1,4,9a-trimethyl-5,11-dioxo-1H, 5H-imidazo[4,5-f]pyrrolo[2,1-b][1,3,5]-oxadiazocine hydrochloride (9・HCl) derived from a urea derivative (3a) afforded 4a and 1,4-dimethyl-4,5-dihydro-5,7-dioxo-1H, 7H-imidazo[4,5-d][1,3]oxazine (11). Many of these compounds (4,7 and 8) showed relaxing activity against KCl-induced contraction of arterial strips isolated from the rabbit mesenterium, and potent activity was observed in the case of 71.
公益社団法人日本薬学会の論文
1986-01-25