Calcium Channel Antagonists as Antioxidants

Rojstaczer, Nurit; Triggle, David J.

doi:10.1111/j.1527-3466.1994.tb00284.x

Cited by 8 publications

(3 citation statements)

References 76 publications

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“…They concluded that these Ca 2+ antagonists either singly or in combination might be useful in preventing vasoocclusive events. Ca channel antagonists were shown to act as antioxidant [15]. Calcium antagonists antioxidant potency correlated directly with the compound's relative affinity for the membrane lipid bilayer [16].…”

Section: Resultsmentioning

confidence: 99%

Effect of calcium and diltiazem on phenylhydrazine-induced oxidative injury in goat erythrocytes

Das¹,

Bhattacharyya²

2010

Health

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Lipid peroxidation, hemolysis and thiol contents were studied in intact goat erythrocytes exposed to phenylhydrazine. An increase in lipid peroxidation, hemolysis and thiol content was observed after phenylhydrazine treatment of erythrocyte. Extracellular Ca2+ potentiates the phenylhydrazine-induced lipid peroxidation and hemoly- sis of erythrocytes significantly. Ca2+ does not influence much the thiol content of phenylhydrazine treated erythrocytes. No effect of Ca2+ on control lipid peroxidation, hemolysis and thiol contents of erythrocytes was observed. Diltiazem and EDTA inhibited the increased responses of lipid peroxidation and hemolysis due to Ca2+. However the thiol content was not much influenced by either diltiazem or EDTA. The results suggest that oxidative damage of erythrocyte caused by phenyl hydrazine could be prevented by calcium channel antagonist, diltiazem, which may act as antioxidant also

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Section: Resultsmentioning

confidence: 99%

Effect of calcium and diltiazem on phenylhydrazine-induced oxidative injury in goat erythrocytes

Das¹,

Bhattacharyya²

2010

Health

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“…1,4-Dihydropyridines (DHPs) are known as effective calcium antagonists and many cardiovascular drugs on their basis are now used in the clinics or still are in different stages of development [1][2][3][4]. 6-Alkylthio-1,4-DHPs display cardiovascular [5,6], hepatoprotective [7], antioxidant (AOA) [8], and antiradical (ARA) [9] activity, however, these compounds are still insufficiently studied pharmacologically.…”

Section: Introductionmentioning

confidence: 99%

Green One-Pot Multicomponent Synthesis of 4-Aryl-6-Carbamoylmethylthio-5-Cyano-2-Methyl-1,4-Dihydropyridine-3-Carboxylic Acid Methyl Esters

Krauze¹,

Chernova²,

Vilums³

et al. 2006

Heterocyclic Communications

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4-Aryl-6-carbamoylmethylthio-5-cyano-2-methyl-l ,4-dihydropyridine-3-carboxylic acid methyl esters 7 were obtained by an one-pot condensation of 2-(3-chloro-or 2,4-dichlorobenzylidene)-3oxobutyric acid methyl esters and 2-cyanothioacetamide in the presence of stoichiometric amount of piperidine or ammonium hydroxide with subsequent alkylation with iodoacetamide or chloroacetamide. Application of ammonium hydroxide instead of piperidine and much cheaper chloroacetamide instead of iodoacetamide does not influence significantly the yield of reactions, but makes this method greener: gives rise to environmentally friendly waste product -ammonium chloride and 22-23 % atom economy.

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“…Antihypertensive properties are often exhibited by α 1 -adrenoreceptor blockers. Thus combining in a single molecule 1,4-dihydropyridine groups (calcium antagonists with antihypertensive properties) [9,10]) with potential α1-adrenoreceptor ligands may lead to new biologically active compounds.…”

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confidence: 99%

Synthesis and Properties of 7-Acetyl-8-aryl-9-cyano-3-hydroxy-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines

Krauze

Sile

Danne

et al. 2005

Chem Heterocycl Compd

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Based on our early studies of the reaction of 1,4-dihydropyridine-2(3H)-thiolates with electrophilic reagents [1-3], we used the reactions of 5-acetyl-4-aryl-3-cyano-6-methyl-1,4-dihydropyridine-2(3H)-thiones with electrophilic epichlorohydrin for synthesis of 2-(1,2-dihydroxy-3-propyl)thio-1,4-dihydropyridines, mimetics of glyceride derivatives of 1,4-dihydropyridines, and their cyclic analogs: acylated and hydrogenated pyrido[2,1-b][1,3]thiazines.Although 3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines have been poorly studied, their synthesis is of interest since the combination in one molecule of a 1,4-dihydropyridine ring (calcium antagonists, antioxidants, hepatoprotectors) and a 1,3-thiazine ring (antibiotics of the cephalosporin group) can lead to potential biologically active compounds. Antihypertensive and anti-inflammatory activities have been found in the corresponding hydrogenated pyrido[2,1-b][1,3]oxazines [4].1,4-Dihydropiperidine-2(3H)-thiones 1 were obtained by two routes: thione 1a [5] and thione 1b by condensation of acetylacetone, an aromatic aldehyde, and 2-cyanothioacetamide; and thione 1c [6] by reaction of 2-(3-nitrophenyl)methyleneacetylacetone with 2-cyanothioacetamide in the presence of an equimolar amount of piperidine followed by acidification.5-Acetyl-4-aryl-2-(1-chloro-2-hydroxy-3-propyl)thio-3-cyano-6-methyl-1,4-dihydropyridines 2 were obtained in moderate yields by treatment of compound 1 with epichlorohydrin in the presence of sodium bicarbonate. When using stronger bases (KOH or NaOMe) instead of sodium bicarbonate, the 7-acetyl-8-aryl-9-cyano-3-hydroxy-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines 3 crystallize out from a complex reaction medium in 50%-59% yields. Compounds 3 were also obtained in 62-69% yields by intramolecular alkylation of compounds 2 by treatment with NaOMe at room temperature.

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Calcium Channel Antagonists as Antioxidants

Cited by 8 publications

References 76 publications

Effect of calcium and diltiazem on phenylhydrazine-induced oxidative injury in goat erythrocytes

Effect of calcium and diltiazem on phenylhydrazine-induced oxidative injury in goat erythrocytes

Green One-Pot Multicomponent Synthesis of 4-Aryl-6-Carbamoylmethylthio-5-Cyano-2-Methyl-1,4-Dihydropyridine-3-Carboxylic Acid Methyl Esters

Synthesis and Properties of 7-Acetyl-8-aryl-9-cyano-3-hydroxy-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines

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