67448-14-0

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 2-(dimethoxymethyl)-1,4-dihydro-6-methyl-4-(2-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester
• CAS NO: 67448-14-0
• Molecular Formula: C21H26N2O8
• Molecular Weight: 434.446
• Mol File: 67448-14-0.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 2-(dimethoxymethyl)-1,4-dihydro-6-methyl-4-(2-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 2-(dimethoxymethyl)-1,4-dihydro-6-methyl-4-(2-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester(67448-14-0)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 2-(dimethoxymethyl)-1,4-dihydro-6-methyl-4-(2-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester(67448-14-0)

Safety Data

• Hazardous Substances Data: 67448-14-0(Hazardous Substances Data)

Upstream product

• 14205-46-0 isopropyl 3-aminocrotonate 
• 67448-12-8 4,4-Dimethoxy-2-[1-(2-nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester 
• 40100-28-5 isopropyl 3-aminocrotonate 
• 60705-25-1 4,4-dimethoxy-3-oxo-butyric acid methyl ester 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 67448-23-1 isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 
• 67448-29-7 isopropyl 2-methyl-4-(2-nitrophenyl)-5-methoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate 
• 67448-36-6 isopropyl 2-methyl-4-(2-nitrophenyl)-5-methoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate 

Relevant articles and documents

A simple and expeditious synthesis of substituted 3-aminoindolizines

Treatment of easily available 2-formyl-1,4-dihydropyridines with 3-oxo-3-phenylpropanenitrile offers a simple and efficient one-pot method for the preparation of substituted 3-amino-indolizines.

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.

1,4-Dihydropyridine derivatives, and pharmaceutical method of the same

1,4-dihydropyridine derivatives of the general formula STR1 having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.