75530-94-8

Basic information

• Product Name: 4-(3-Nitrophenyl)-2-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester
• Synonyms: 4-(3-Nitrophenyl)-2-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester;2-(DiMethoxyMethyl)-1,4-dihydro-6-Methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl 5-(1-Methylethyl) Ester
• CAS NO: 75530-94-8
• Molecular Formula: C₂₁H₂₆N₂O₈
• Molecular Weight: 420
• Product Categories: Chemical Amines;Amines;Aromatics;Drug Analogues;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Dihydropyridine
• Mol File: 75530-94-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(3-Nitrophenyl)-2-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Nitrophenyl)-2-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester(75530-94-8)
• EPA Substance Registry System: 4-(3-Nitrophenyl)-2-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester(75530-94-8)

Safety Data

• Hazardous Substances Data: 75530-94-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Liquid

Uses

4-(3-Nitrophenyl)-2-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester (cas# 75530-94-8) is a compound useful in organic synthesis.

Upstream product

• 40100-28-5 isopropyl 3-aminocrotonate 
• 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 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 75530-61-9 isopropyl 2-hydroxymethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3-methoxycarbonyl-5-piperidinecarboxylate 
• 75530-68-6 nilvadipine 
• 75530-60-8 isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 

Relevant articles and documents

Conformationally constrained 1,4-DHPs. A convenient route to bis-1,4-DHPs as a novel class of nitrogen compounds

2-Formyl-1,4-DHP derivatives 2 undergo the tandem Knoevenagel condensation/amino-nitrile cyclisation with activated methylene reagents to afford high functionalised indolizines. However, in the absence of this tandem, the Knoevenagel condensation intermediate leads to bis-1,4-DHPs as a new class of nitrogen compounds.

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.