Formation and decay of free cation-radicals in the course of electro-oxidation of 1,2- and 1,4-dihydropyridines (Hantzsch esters)

Ogle, John J.; Stradins, J.; Баумане, Л.

doi:10.1016/0013-4686(94)85011-9

Cited by 31 publications

(16 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…DHPs form free radicals in chemical, electrochemical, and biological oxidation processes. The kinetic parameters and pathways of decay of the cationic radicals formed as primary products in the course of electrooxidation of the esters of 1,2- and 1,4-dihydropyridine have been extensively studied [ 76 ].…”

Section: 14-dihydropyridines: a Separate Group Of Bioantioxidantsmentioning

confidence: 99%

1,4‐Dihydropyridine Derivatives: Dihydronicotinamide Analogues—Model Compounds Targeting Oxidative Stress

Velēna

Žarković

Trošelj

et al. 2016

Oxidative Medicine and Cellular Longevity

View full text Add to dashboard Cite

Many 1,4-dihydropyridines (DHPs) possess redox properties. In this review DHPs are surveyed as protectors against oxidative stress (OS) and related disorders, considering the DHPs as specific group of potential antioxidants with bioprotective capacities. They have several peculiarities related to antioxidant activity (AOA). Several commercially available calcium antagonist, 1,4-DHP drugs, their metabolites, and calcium agonists were shown to express AOA. Synthesis, hydrogen donor properties, AOA, and methods and approaches used to reveal biological activities of various groups of 1,4-DHPs are presented. Examples of DHPs antioxidant activities and protective effects of DHPs against OS induced damage in low density lipoproteins (LDL), mitochondria, microsomes, isolated cells, and cell cultures are highlighted. Comparison of the AOA of different DHPs and other antioxidants is also given. According to the data presented, the DHPs might be considered as bellwether among synthetic compounds targeting OS and potential pharmacological model compounds targeting oxidative stress important for medicinal chemistry.

show abstract

Section: 14-dihydropyridines: a Separate Group Of Bioantioxidantsmentioning

confidence: 99%

1,4‐Dihydropyridine Derivatives: Dihydronicotinamide Analogues—Model Compounds Targeting Oxidative Stress

Velēna

Žarković

Trošelj

et al. 2016

Oxidative Medicine and Cellular Longevity

View full text Add to dashboard Cite

show abstract

“…The more detailed mechanistic information has been obtained in aprotic media [11][12][13][14][15][16][17][18]. These investigations were generally done by using mainly rotating ring disk electrode (RRDE), linear and cyclic voltammetry and ESR spectroscopy, and have revealed that, in non-aqueous solutions, 1,4-dihydropyridine derivatives are oxidized in a two electron reaction, in particular, in an ECEC mechanism type.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation of C4-vanillin- and C4-isovanillin-1,4-dihydropyridines in aprotic medium: Reactivity towards free radicals

Salazar

Navarrete-Encina

Camargo

et al. 2008

Journal of Electroanalytical Chemistry

View full text Add to dashboard Cite

“…Antioxidant properties have also been confirmed for the heterocycle itself in reactions with various radicals [6,7]. On the other hand study of the redox reaction of the dihydropyridine ring is also important for the reason that its oxidation is the main metabolism of dihydropyridines.The attention of electrochemists is mainly attracted [8][9][10][11][12][13] by the oxidation of 4-methyl-, 4-aryl-1,4-dihydropyridines or those unsubstituted in position 4. In all the mentioned cases proton is split off from the position 4 of the ring on oxidation.…”

mentioning

confidence: 99%

“…The attention of electrochemists is mainly attracted [8][9][10][11][12][13] by the oxidation of 4-methyl-, 4-aryl-1,4-dihydropyridines or those unsubstituted in position 4. In all the mentioned cases proton is split off from the position 4 of the ring on oxidation.…”

mentioning

confidence: 99%

Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines

Turovska

Goba

Turovskis

et al. 2008

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

The electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines has been studied in an aprotic medium and in the presence of pyridine. In an aprotic medium the products of oxidation are both 4-alkyl-substituted and 4-unsubstituted pyridines or mixtures of them. On oxidation in acetonitrile of 4- 2,3, were obtained in addition to the oxidized forms. In the presence of base the products of preparative electrolysis of the studied compounds were 4-alkyl-substituted pyridines. The exception was the 4-i-Prsubstituted dihydropyridine which was dealkylated on oxidation even in the presence of base.Dihydropyridines are one of the most investigated classes of organic compounds. The synthesis and reactions of 1,4-dihydropyridines have been examined in detail in reviews [1][2][3][4]. Many compounds of this series possess pharmacological activity. A series of pharmaceuticals [5] has been developed based mainly on 4-arylsubstituted 1,4-dihydropyridines. Antioxidant properties have also been confirmed for the heterocycle itself in reactions with various radicals [6,7]. On the other hand study of the redox reaction of the dihydropyridine ring is also important for the reason that its oxidation is the main metabolism of dihydropyridines.The attention of electrochemists is mainly attracted [8][9][10][11][12][13] by the oxidation of 4-methyl-, 4-aryl-1,4-dihydropyridines or those unsubstituted in position 4. In all the mentioned cases proton is split off from the position 4 of the ring on oxidation. N Me H Me R H COOMe MeOOC 1-5 1 R = Me, 2 R = Et, 3 R = n-Pr, 4 R = i-Pr, 5 R = i-Bu

show abstract

Formation and decay of free cation-radicals in the course of electro-oxidation of 1,2- and 1,4-dihydropyridines (Hantzsch esters)

Cited by 31 publications

References 5 publications

1,4‐Dihydropyridine Derivatives: Dihydronicotinamide Analogues—Model Compounds Targeting Oxidative Stress

1,4‐Dihydropyridine Derivatives: Dihydronicotinamide Analogues—Model Compounds Targeting Oxidative Stress

Electrochemical oxidation of C4-vanillin- and C4-isovanillin-1,4-dihydropyridines in aprotic medium: Reactivity towards free radicals

Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines

Contact Info

Product

Resources

About