N1-Alkylated 3,4-dihydropyrimidine-2(1 H)-ones: Convenient one-pot selective synthesis and evaluation of their calcium channel blocking activity

It has been found that selective N1-alkylation of 3,4-dihydropyrimidine-2(1 H)-ones can be achieved under solvent-less, mild phase transfer catalytic (PTC) conditions with tetrabutylammonium hydrogen sulfate and 50% aqueous NaOH as the catalyst and base, respectively. The procedure is tolerant to su...

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Bibliographic Details
Published in:	European journal of medicinal chemistry Vol. 44; no. 5; pp. 1997 - 2001
Main Authors:	Singh, Kamaljit, Arora, Divya, Poremsky, Elizabeth, Lowery, Jazmyne, Moreland, Robert S.
Format:	Journal Article
Language:	English
Published:	Kidlington Elsevier Masson SAS 01-05-2009 Elsevier
Subjects:	Alkylation Antihypertensive agents Biginelli dihydropyrimidinones Biological and medical sciences Calcium Channel Blockers - chemical synthesis Calcium Channel Blockers - pharmacology Cardiovascular system Catalysis Humans Medical sciences N-Alkylation Pharmacology. Drug treatments Phase transfer catalysis Pyrimidinones - chemical synthesis Pyrimidinones - pharmacology Regioselective Tetrabutylammonium hydrogen sulfate Vascular smooth muscle Phase transfer catalysis N-Alkylation Regioselective Biginelli dihydropyrimidinones Tetrabutylammonium hydrogen sulfate Vascular smooth muscle Vasodilator agent Regioselectivity Nitrogen heterocycle Calcium antagonist Selectivity Pyrimidone derivatives In vitro Alkylation Ester Structure activity relation Solvent free Six membered ring Antihypertensive agent Ureas Biginelli reaction Chemical synthesis
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Summary:	It has been found that selective N1-alkylation of 3,4-dihydropyrimidine-2(1 H)-ones can be achieved under solvent-less, mild phase transfer catalytic (PTC) conditions with tetrabutylammonium hydrogen sulfate and 50% aqueous NaOH as the catalyst and base, respectively. The procedure is tolerant to substitutional variation at key diversity points on the pyrimidinone moiety. N1-Alkylation of 3,4-dihydropyrimidine-2(1 H)-ones can be achieved under solvent-less, mild phase transfer catalytic (PTC) conditions with tetrabutylammonium hydrogen sulfate and 50% aqueous NaOH as the catalyst and base, respectively. N1-Substituted DHPM derivatives show moderate calcium channel blocking activity. [Display omitted]
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0223-5234 1768-3254
DOI:	10.1016/j.ejmech.2008.10.002