75530-61-9

Upstream product

• 75530-60-8 isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 
• 191742-12-8 isopropyl 2-acetoxymethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3-methoxycarbonyl-5-piperidinecarboxylate 
• 14205-46-0 isopropyl 3-aminocrotonate 
• 99-61-6 3-nitro-benzaldehyde 
• 87730-99-2 4-acetoxy-3-oxo-butyric acid methyl ester 
• 75530-94-8 isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 
• 67448-15-1 (E,Z)-methyl 4,4-dimethoxy-2-(3-nitrobenzylidene)acetoacetate 
• 60705-25-1 4,4-dimethoxy-3-oxo-butyric acid methyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of (R)-nilvadipine and (S)-NB 818 via regioselective bromination of chiral 1,4-dihydropyridines as a key step and enzymatic resolution of racemic 2-hydroxymethyl-1,4-dihydropyridine derivatives

Optically active 2-hydroxymethyl-1,4,dihydropyridines were obtained by lipase-catalyzed hydrolysis or transesterification of racemic materials. Chiral NB 818 and nilvadipine have been synthesized from chiral 2- hydroxymethyl-1,4-dihydropyridine. On the ot

Studies on nilvadipine. I. Synthesis and structure-activity relationships of 1,4-dihydropyridines containing novel substituents at the 2-position

The synthesis of new 1,4-dihydropyridine derivatives containing novel substituent at the 2-position of the nucleus via the key intermediate 2-formyl-1,4-dihydropyridines (X), is described. The aldehydes (X) were prepared by hydrolysis of the acetals (IX) which were obtained from aryl aldehyde (V) and alkyl 4,4-dialkoxyacetoacetate (VI) by the Knoevenagel reaction and treatment with alkyl 3-aminocrotonate (VIII) according to the modified Hantzsch method. The formyl group of the aldehydes (X) was reactive enough to be converted to a variety of functional groups such as hydroxymethyl, cyano, substituted iminomethyl, carbamoyl, semicarbazone, substituted vinyl, ethynyl, and so on. In all of the novel compounds we prepared, 2-hydroxymethyl- and 2-cyano-1,4-dihydropyridines (IV and XXII) were found to possess potent activities in preliminary biological evaluations on hypotension in normotensive rats and on an increase in coronary blood flow in pentobarbital-anesthetized dogs. Optimization research in order to obtain a more potent compound was accomplished in the 2-hydroxymethyl- and 2-cyano-1,4-dihydropyridine series. We selected isopropyl 2-cyano-3-methoxycarbonyl-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridin e-5-carboxylate (XXIIj) as a candidate compound for further biological evaluation studies. Fortunately, XXIIj (nilvadipine) has been accepted in clinical use for the treatment of hypertension.