Abstract
Proceeding from natural amino acid L-asparagine and commercially available aldehydes a stereoselective synthesis was developed of (2S,4S)-2-alkyl(aryl)-3-(3-sulfanylpropanoyl)-6-oxohexahy- dropyrimidine-4-carboxylic acids, potential antihypertensive drugs, inhibitors of the angiotensin converting enzyme.
Highlights
Efficient antihypertensive drugs function as inhibitors of the angiotensin converting enzyme (ACE)
In the series of the saturated pyrimidine derivatives the only example of the inhibitor activity with respect to ACE is known to be shown by 3-(3-sulfanylpropanoyl)-6-oxohexahydropyrimidine-4-carboxylic acid [11]
It was found by the analysis of published data that sodium salts of 2-substituted 6-oxohexahydropyrimidine-4-carboxylic acids formed in the reaction of the natural amino acid L-asparagine with carbonyl compounds in alkaline medium
Summary
Efficient antihypertensive drugs function as inhibitors of the angiotensin converting enzyme (ACE). In the series of the saturated pyrimidine derivatives the only example of the inhibitor activity with respect to ACE is known to be shown by 3-(3-sulfanylpropanoyl)-6-oxohexahydropyrimidine-4-carboxylic acid [11] It was found by the analysis of published data that sodium (potassium) salts of 2-substituted 6-oxohexahydropyrimidine-4-carboxylic acids formed in the reaction of the natural amino acid L-asparagine with carbonyl compounds in alkaline medium. This reaction was investigated mainly by an example of derivatives of isobutyric, trimethylacetic, and benzoic aldehydes [12]-[16]. The process was found to occur with a high stereoselectivity giving prevailingly the spatial isomer with (2R,4S)-configuration of the substituents in the pyrimidine ring
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