62760-70-7

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl 2-(hydroxymethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate is used as a potential vasodilator and anti-hypertensive agent for the treatment of cardiovascular diseases. Its dihydropyridine structure suggests that it may have similar pharmacological effects as other dihydropyridines, which are commonly used in the management of hypertension and angina.
Used in Research and Development:
diethyl 2-(hydroxymethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate is used in research and development for the investigation of its biological and pharmacological activities. Further studies are needed to explore its potential uses and effects, which may lead to the development of new therapeutic agents for various medical conditions.

Upstream product

• 62760-23-0 diethyl 2-methyl-4-(3-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 99-61-6 3-nitro-benzaldehyde 
• 62759-88-0 diethyl 2-diethoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 10495-09-7 ethyl 4,4-diethoxyacetoacetate 
• 62759-87-9 (E,Z)-ethyl 4,4-diethoxy-2-(3-nitrobenzylidene)acetoacetate 

Downstream Products

• 62760-94-5 diethyl-2-acetoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 105435-14-1 2-chloromethyl-3,5-dicarboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine 
• 110645-72-2 diethyl 6-methyl-2-(1-methyltetrazol-5-yl)thiomethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 89267-47-0 ethyl-2-methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,7-tetrahydrofuro<3,4-b>-3-pyridinecarboxylate 
• 74666-23-2 2-Methyl-4-(3-nitro-phenyl)-6-(pyridine-3-carbonyloxymethyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels CaV1.3 and CaV1.2

L-type Ca2+ channels in mammalian brain neurons have either a CaV1.2 or CaV1.3 pore-forming subunit. Recently, it was shown that CaV1.3 Ca2+ channels underlie autonomous pacemaking in adult dopaminergic neurons in the substantia nigra pars compacta, and this reliance renders them sensitive to toxins used to create animal models of Parkinson's disease. Antagonism of these channels with the dihydropyridine antihypertensive drug isradipine diminishes the reliance on Ca2+ and the sensitivity of these neurons to toxins, pointing to a potential neuroprotective strategy. However, for neuroprotection without an antihypertensive side effect, selective CaV1.3 channel antagonists are required. In an attempt to identify potent and selective antagonists of CaV1.3 channels, 124 dihydropyridines (4-substituted-1,4-dihydropyridine-3,5-dicarboxylic diesters) were synthesized. The antagonism of heterologously expressed CaV1.2 and CaV1.3 channels was then tested using electrophysiological approaches and the FLIPR Calcium 4 assay. Despite the large diversity in substitution on the dihydropyridine scaffold, the most CaV1.3 selectivity was only about twofold. These results support a highly similar dihydropyridine binding site at both CaV1.2 and CaV1.3 channels and suggests that other classes of compounds need to be identified for CaV1.3 selectivity.

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.

6-Acyloryalkyl-1,4-dihydropyridine derivatives and a method of effecting vasodilation therewith

This invention relates to 1,4-dihydropyridine derivatives. More particularly, it relates to new 1,4-dihydropyridine derivatives thereof which have vasodilating and anti-hypertensive activity, to processes for the preparation thereof, and to pharmaceutical composition comprising the same for therapeutical treatment in cardiovascular diseases and hypertension in human being.