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Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds

“…DHPs have many biological features included vasodilator, antihypertensive, bronchodilator, antiatherosclerotic, anticonvulsant, hepatoprotective, antitumor, antimutagenic, geroprotective, antidiabetic, antioxidant, antiradical and controlling cellular proliferation [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]. Although DHP's have been developed as cardiovascular agents some of them have been used for other medical applications.…”

Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

“…4-H, 3 J = 3.6 Hz),6.86 s (1H, OH),6.99 s (2H, H arom ), 7.78 d (1H, 3-H).13 C NMR spectrum (100 MHz), δ C , ppm: 14.19 (CH 3 ), 16.01 (6-CH 3 ), 29.63 (1-CH 3 ), 30.32 [(CH 3 ) 3 C], 34.54 [(CH 3 ) 3 C], 52.46 (C 4 ), 59.58 (CH 2 O), 103.95 (C 5 ), 122.06 (C 9 , C 11), 135.42 (C 7 ), 139.07 (C 8 , C 12 ), 149.60 (C 6 ), 153.05 and 153.70 (C 2 , C 10 ), 165.82 (5-CO). Mass spectrum, m/z (I rel , %): 402 (31.5) [M] + , 387 (15.9) [M -Me] + , 373 (85.1) [MEt] + , 345 (23.3) [M -Bu] + , 329 (51.4) [M -COOEt] + , 197 (100) [M -Ar] + , 169 (26.8), 151 (28.5) [M -ArEtOH] + , 124 (9.4) [M -Ar -COOEt] + .…”

“…Heterocyclic compounds containing a 3,5-di-tert-butyl-4-hydroxyphenyl group have been reported to exhibit antioxidant activity in combination with other kinds of biological activity. Examples are calcium channel antagonists of the 1,4-dihydropyridine [6] and thiazolidinone series [7], antisclerotic agents of the oxadiazole series [8], and lipoprotein oxidation inhibitors of the dihydropyrazole series [9]. Compounds possessing antioxidant properties were found among 4-aryl-3,4-dihydropyrimidin-2-one derivatives substituted at the 5-position with an alkoxycarbonyl group having both simple and bulky alkyl radicals [10].…”

Synthesis, Structure, and Electrochemical Characteristics of 4-Aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic Acid Nitriles

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Keywords: 1,4-dihydropyridines, hydrogen bond, one-pot multicomponent method, electrochemical oxidation, X-ray diffraction analysis.Nitriles of 2-alkylthio-4-aryl-1,4-dihydropyridine-3-carboxylic acids are of interest as potential antioxidants [1,2] that are also distinguished by cardiovascular [3,4] and hepatoprotective [5] activity.Continuing a study of the chemical and electrochemical properties of 2-alkylthio-1,4-dihydropyridines [4, 6] and methods for obtaining them [7,8], we have synthesized a series of novel 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-6-methyl-1,4-dihydropyridine-3-carboxylic acid nitriles 1, in which we varied the substituents on the 4-phenyl ring over a broad range. We carried out a comparative analysis of the capability for electrochemical oxidation of 2-alkylthio-4-aryl-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles 1 and 4 as a function of the electronic properties of the aryl substituent on the 4 position of the heterocycle and the 2-alkylthio substituent, since the corresponding values of the potentials quantitatively characterize the antioxidant properties of the compounds.

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“…Nitriles of 2-alkylthio-4-aryl-1,4-dihydropyridine-3-carboxylic acids are of interest as potential antioxidants [1,2] that are also distinguished by cardiovascular [3,4] and hepatoprotective [5] activity.…”