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

Баумане, Л.; Krauze, A.; Belyakov, Sergey; Sile, L.; Chernova, L.; Griga, M.; Дубурс, Г.; Stradins, J.

doi:10.1007/s10593-005-0156-x

Cited by 10 publications

(3 citation statements)

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“…The multicomponent (cascade, tandem) reactions of cyanothioacetamide, the order of their stages, and the proposed mechanisms were analyzed earlier in the reviews [1, [5][6][7][8]14]. On account of the experimental convenience and technological effectiveness multicomponent reactions were developed further in [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. The advantages of the condensations include the possibility of producing derivatives of 3-cyanopyridine-2-thione [44][45][46][47][48][49][50][51][52], polysubstituted thiazoles [52] and thiophenes [53], and polycyclic heterosystems containing a pyridine ring [54][55][56][57][58][59][60][61] in one pot.…”

Section: Unusual Two-component Heterocyclizations Of Cyanothioacetamidementioning

confidence: 99%

“…The pyridine-3-carbonitriles 62 and 63 were obtained by the multicomponent reaction of compounds 1, 60, and 61 [46][47][48][49], and their cardiovascular activity [48] and electrochemical oxidation [47][48][49] were investigated. It was found that the derivatives of 1,4,5,6-tetrahydropyridine 62 are as a rule oxidized more readily than the corresponding 1,4-dihydropyridines 63.…”

Section: Mementioning

confidence: 99%

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Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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Data from the last six years on the heterocyclization of thioamides containing an active methylene group are analyzed and classified.At the present time there has been a considerable increase in the number of publications on the chemistry of thioamides, and this is explained by the value of the compounds as initial reagents for further transformations and particularly for the synthesis of various sulfur-and nitrogen-containing heterocycles [1][2][3][4][5][6][7][8]. The enormous practical significant of the latter is common knowledge -they have found application as drugs, pesticides, dyes, and preservatives.Thioamides with an active methylene group are attractive synthesis units for the production of heterocycles. These polyfunctional compounds can be represented by the formula R 3 -CH 2 CS-NR 1 R 2 (where R 1 , R 2 = H, Alk, Ar; R 3 is an electron-withdrawing group such as CN, AlkCO, ArCO, (AlkO) 2 PO, AlkSO 2 , ArSO 2 , NO 2 ). The presence of another reaction center (the methylene group) makes it possible to use them as N-С-С and S-C-C components for various condensations [1][2][3][4][5][6][7][8]. A special feature of such substrates is the ability to react both with dinucleophilic and with dielectrophilic and dipolar reagents. As a rule the products of these heterocyclizations contain functional groups, which makes it possible to achieve their modification or annelation. Such characteristics of thioamides with an active methylene group substantially increase their synthetic potential and extend the range of accessible heterosystems, while the use of modern physical methods of investigation (X-ray crystallographic analysis and 1D and 2D NMR spectroscopy) makes it possible to establish the structure of the obtained compounds unambiguously. The presence of biological activity in the products of these transformations also attracts investigators to this subject [5][6][7][8].The reason for the appearance of this review was the increasing need for generalization and classification of new information on the heterocyclization of such thioamides that had not been included in previous reviews [2][3][4][5] and also to define the trends in the study of these processes. Since one of the most important reports in this field is the review [1] we undertook an analysis of the literature that has appeared in the last six years.

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Section: Unusual Two-component Heterocyclizations Of Cyanothioacetamidementioning

confidence: 99%

Section: Mementioning

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…The electrochemical oxidation of various 1,4-dihydropyridine derivatives has been extensively studied [ 46 – 50 ] including 1,4-DHP derivatives containing cationic moieties [ 29 , 44 ]. The electrochemical oxidation of the selected compounds studied in this work was performed by cyclic voltammetry on a stationary glassy carbon electrode in dry acetonitrile; the data is presented in Table 4 .…”

Section: Resultsmentioning

confidence: 99%

Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds

Ruciņš

Smits

Sipola

et al. 2020

Oxidative Medicine and Cellular Longevity

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Three groups of synthetic lipids are chosen for studies: (1) 1,4-dihydropyridines (1,4-DHPs) containing two cationic moieties and their analogues; (2) 3,4-dihydro-2(1H)-pyridones containing a cationic moiety; and (3) acyclic, open-chain analogues, i.e., 2-amino-3-alkoxycarbonylalkylammonium derivatives. 1,4-DHPs possessing dodecyl alkyl chains in the ester groups in positions 3 and 5 and cationic nitrogen-containing groups in positions 2 and 6 have high cytotoxicity in cancer cells HT-1080 (human lung fibrosarcoma) and MH-22A (mouse hepatoma), but low cytotoxicity in the noncancerous NIH3T3 cells (mouse embryonic fibroblast). On the contrary, similar compounds having short (methyl, ethyl, or propoxyethyl) chains in the ester groups in positions 3 and 5 lack cytotoxicity in the cancer cells HT-1080 and MH-22A even at high doses. Inclusion of fluorine atoms in the alkyl chains in positions 3 and 5 of the DHP cycle decreases the cytotoxicity of the mentioned compounds. Structurally related dihydropyridones with a polar head group are substantially more toxic to normal and cancerous cells than the DHP analogues. Open-chain analogues of DHP lipids comprise the same conjugated aminovinylcarbonyl moiety and possess anticancer activity, but they also have high basal cytotoxicity. Electrochemical oxidation data demonstrate that oxidation potentials of selected compounds are in the range of 1.6–1.7 V for cationic 1,4-DHP, 2.0–2.4 V for cationic 3,4-dihydropyridones, and 1.2–1.5 V for 2-amino-3-alkoxycarbonylalkylammonium derivatives. Furthermore, the tested cationic 1,4-DHP amphiphiles possess antiradical activity. Molecular topological polar surface area values for the tested compounds were defined in accordance with the main fragments of compound structures. The determined log P values were highest for dodecyl ester groups in positions 3 and 5 of the 1,4-DHP and lowest for short alkyl chain-containing amphiphiles.

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