Imidazo[1,5- a]pyrimidine and benzo[4,5]imidazo[1,2- a]pyrimidine derivatives as calcium antagonists

Several bicyclic dihydropyrimidines were synthesized and evaluated for their calcium antagonistic activities by comparison with the usual 1,4-dihydropyridine calcium antagonist reference compound nifedipine. The solid-state structure of the isopropyl 2-methyl-4-(3′-nitrophenyl)-1,4-dihydrobenzo[4,5]...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1994-05, Vol.2 (5), p.323-329
Main Authors: Alajarin, Ramón, Vaquero, Juan J., Alvarez-Builla, Julio, de Casa-Juana, Miguel Fau, Sunkel, Carlos, Priego, Jaime G., Gomez-Sal, Pilar, Torres, Rosario
Format: Article
Language:English
Subjects:
Animals
Aorta, Thoracic - drug effects
Calcium Channel Blockers - chemical synthesis
Calcium Channel Blockers - chemistry
Calcium Channel Blockers - pharmacology
Crystallography, X-Ray
Drug Evaluation, Preclinical
In Vitro Techniques
Magnetic Resonance Spectroscopy
Male
Models, Molecular
Molecular Structure
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Pyrimidines - pharmacology
Rats
Rats, Sprague-Dawley
Vasodilator Agents - chemical synthesis
Vasodilator Agents - chemistry
Vasodilator Agents - pharmacology
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Summary:Several bicyclic dihydropyrimidines were synthesized and evaluated for their calcium antagonistic activities by comparison with the usual 1,4-dihydropyridine calcium antagonist reference compound nifedipine. The solid-state structure of the isopropyl 2-methyl-4-(3′-nitrophenyl)-1,4-dihydrobenzo[4,5]imidazo[1,2- alpyrimido-3-carboxylate shows that these compounds can adopt the most important structural features of the 1,4-dihydropyridine and 1,4-dihydropyrimidine calcium channel blockers. The high-potassium depolarized rat aorta assay was used for testing the compounds as calcium channel blockers. Some compounds showed interesting vasorelaxant activity. Several imidazo[1,5-a]pyrimidine and benzo[4,5]imidazo[1,2-a]pyrimidine derivatives were synthesized and evaluated as calcium antagonists. Structural and conformational aspects were studied by X-ray analysis.
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(00)82188-4