62760-65-0Relevant academic research and scientific papers
Synthesis of unsymmetrical 1, 4-dihydropyridine derivatives in ionic liquid and inference on the formation mechanism of furopyridines
Zhang, Jian,Jin, Long Fei
, p. 916 - 921 (2012/02/16)
Aromatic aldehydes, methyl acetoacetate, ethyl acetoacetate, ammonium acetate, ethyl 4-chloroacetoacetate as materials, eight unsymmetrical 1, 4-dihydropyridine derivatives were synthesized in ionic liquid [Bmim]OH in short time with the 60%-90% yield, and the ionic liquid could be utilized for 5 times repeatedly with the no decrease of the yield, four of products [3(a-d)] (see in Table-1) were synthesized through Knoevenagel and Michael addition reaction, and another four Furopyridines [3(e-h)] (see in Table-2) through one-pot synthesis whose formation mechanism being different from that of [3(a-d)] was first inferred.
Studies on nilvadipine. I. Synthesis and structure-activity relationships of 1,4-dihydropyridines containing novel substituents at the 2-position
Satoh,Ichihashi,Okumura
, p. 3189 - 3201 (2007/10/02)
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
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, (2008/06/13)
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
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, (2008/06/13)
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.
