Voltamperometry of 1,4-dihydropyridine derivatives

Stradyn, Ya. P.; Beilis, Yu. I.; Uldrikis, Ya. R.; Dubur, G. Ya.; Sausin, A. E.; Chekavichus, B. S.

doi:10.1007/bf00474458

Cited by 4 publications

(2 citation statements)

References 5 publications

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“…These data were also in agreement with our previous results, where the electrochemical oxidation potential of a similar cationic 1,4-DHP was determined as 1.7 V, and the electrochemical oxidation of this compound was characterized as a two-electron process [50], whereas the parent compounds-1,4-DHP derivatives without cationic moieties demonstrated lower electrooxidation potentials. Thus, 4-phenyl substituted Hantzsch 1,4-dihydropyridine had a potential of 1.08 V [51], and other different 4-aryl substituted 1,4-DHPs had potentials around 1.1 V [52], but 4-monoalkyl substituted 1,4-DHPs had oxidation potentials of 1.01-1.03 V, respectively [53].…”

Section: Synthesis Of 14-dhp Derivativesmentioning

confidence: 95%

Evaluation of Physicochemical Properties of Amphiphilic 1,4-Dihydropyridines and Preparation of Magnetoliposomes

et al. 2021

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This study was focused on the estimation of the targeted modification of 1,4-DHP core with (1) different alkyl chain lengths at 3,5-ester moieties of 1,4-DHP (C12, C14 and C16); (2) N-substituent at position 1 of 1,4-DHP (N-H or N-CH3); (3) substituents of pyridinium moieties at positions 2 and 6 of 1,4-DHP (H, 4-CN and 3-Ph); (4) substituent at position 4 of 1,4-DHP (phenyl and napthyl) on physicochemical properties of the entire molecules and on the characteristics of the obtained magnetoliposomes formed by them. It was shown that thermal behavior of the tested 1,4-DHP amphiphiles was related to the alkyl chains length, the elongation of which decreased their transition temperatures. The properties of 1,4-DHP amphiphile monolayers and their polar head areas were determined. The packing parameters of amphiphiles were in the 0.43–0.55 range. It was demonstrated that the structure of 1,4-DHPs affected the physicochemical properties of compounds. “Empty” liposomes and magnetoliposomes were prepared from selected 1,4-DHP amphiphiles. It was shown that the variation of alkyl chains length or the change of substituents at positions 4 of 1,4-DHP did not show a significant influence on properties of liposomes.

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Section: Synthesis Of 14-dhp Derivativesmentioning

confidence: 95%

Evaluation of Physicochemical Properties of Amphiphilic 1,4-Dihydropyridines and Preparation of Magnetoliposomes

et al. 2021

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“…an acid chloride in an inactive DHP amide. 35,36 For this reason, an electron deficient 4-phenyl DHP amide was prepared and this proved stable towards purification by silica gel chromatography (Fig. Initially, we investigated the amide of an unsubstituted DHP (Fig.…”

Section: Introductionmentioning

confidence: 99%

Oxidative activation of dihydropyridine amides to reactive acyl donors

2015

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Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields.

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4-Pyridinio-1,4-Dihydropyridines as Calcium Ion Transport Modulators: Antagonist, Agonist, and Dual Action

Домрачева

Kanepe

Vilšķe̅rsts

et al. 2020

Oxidative Medicine and Cellular Longevity

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A set of six new 4-pyridinio-1,4-dihydropyridine (1,4-DHP) compounds has been synthesized. The calcium channel modulating activity of these compounds was evaluated in an aorta vascular smooth muscle cell line (A7R5), in an isolated rat aortic ring model, and in human neuroblastoma cell lines (SH-SY5Y). The antagonistic effect of these 1,4-DHP was tested by modulating the impact of carbachol-dependent mobilization of intracellular Ca 2+ in SH-SY5Y cells. The intracellular free Ca 2+ concentration was measured in confluent monolayers of SH-SY5Y cells and A7R5 cells with the Ca 2+ -sensitive fluorescent indicator Fluo-4 NW. Only four compounds showed calcium channel blocking activity in SH-SY5Y and A7R5 cells as well as in the aortic ring model. Among them, compound 3 was the most active calcium channel antagonist, which had 3 times higher activity on carbachol-activated SH-SY5Y cells than amlodipine. Two of the compounds were inactive. Compound 4 had 9 times higher calcium agonist activity than the classic DHP calcium agonist Bay K8644. The intracellular mechanism for the action of compound 4 using inhibitor analysis was elucidated. Nicotinic as well as muscarinic receptors were not involved. Sarcoplasmic reticulum (ER) Ca 2+ (SERCA) stores were not affected. Ryanodine receptors (RyRs), another class of intracellular Ca 2+ releasing channels, participated in the agonist response evoked by compound 4. The electrooxidation data suggest that the studied compounds could serve as antioxidants in OS.

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Voltamperometry of 1,4-dihydropyridine derivatives

Cited by 4 publications

References 5 publications

Evaluation of Physicochemical Properties of Amphiphilic 1,4-Dihydropyridines and Preparation of Magnetoliposomes

Evaluation of Physicochemical Properties of Amphiphilic 1,4-Dihydropyridines and Preparation of Magnetoliposomes

Oxidative activation of dihydropyridine amides to reactive acyl donors

4-Pyridinio-1,4-Dihydropyridines as Calcium Ion Transport Modulators: Antagonist, Agonist, and Dual Action

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