Abstract
The alkylation of 3-cyano-1,4-dihydropyridine-2(3H)-thiones or the condensation of an aromatic aldehyde, cyanothioacetamide, acetylacetone, and methyl iodide in the presence of piperidine has given a series of novel 5-acetyl-2-alkylthio-4-aryl-6-methyl-1,4-dihydropyridine-3-carboxylic acid nitriles. A compound was obtained from 3,5-di(tert-butyl)-4-hydroxybenzaldehyde in the molecule of which were combined the active part of the antioxidant ionol and a 1,4-dihydropyridine ring. It was found that, among the compounds synthesized, the highest antiradical activity occurred in a compound having two hydroxyl groups in the 4-phenyl substituent.
Similar content being viewed by others
REFERENCES
D. J. Triggle, Can. J. Physiol. Pharmacol., 68, 1471 (1990).
G. Tirzitis, I. Kirule, and G. Duburs, Fett. Wiss. Technol., 90, 411 (1988).
N. Rojstaczer and D. J. Triggle, Cardiovasc. Drug. Rev., 12, 70 (1994).
W. F. Kauder and J. Watts, Biochem. Pharmacol., 51, 811 (1996).
A. A. Krauze. R. O. Vitolinya, M. R. Romanova, and G. Ya. Dubur, Khim.-Farm. Zh., 22, 955 (1988).
A. A. Krauze. A. G. Odynets, A. A. Verreva, S. K. Germane, A. N. Kozhukhov, and G. Ya. Dubur, Khim.-Farm, Zh., No. 7, 40 (1991).
I. E. Kirule, A. A. Krauze, A. Kh. Velena, D. Yu. Antipova, G. Ya. Arnitsane, I. A. Vutsina, and G. Ya. Dubur, Khim.-Farm. Zh., No. 11/12, 59 (1992).
A. Krauze, J. Popelis, and G. Duburs, Tetrahedron, 54, 9161 (1998).
J. M. C. Gutteridge and B. Halliwell in D. L. Gilbert and C. A. Colton (eds.), Reactive Oxygen Species in Biological Systems, Kluwer Academic / Plenum Publishing, New York (1999).
C. Rice-Evans and N. J. Miller, Methods Enzymol., 234, 279 (1994).
M. Plotnietse, G. Tirzitis, Ya. Uldrikis, Zh. Koronova, D. Tirzite, N. Makarova, and G. Duburs, Khim. Geterotsikl. Soedin., 1358 (1996).
M. Strube, G. R. M. M. Haenen, H. van den Berg, and A. Bast, Free Radical Res., 26, 515 (1997).
A. Krauze, R. Verhe, and G. Duburs, Latv. J. Chem., No. 1/2, 94 (1996).
A. A. Krauze, R. O. Vitolinya, M. R. Romanova, and G. Ya. Dubur, Khim.-Farm. Zh., 22, 548 (1988).
W. Brand-Williams, M. E. Cuvelier, and C. Berset, Lebensm.-Wiss. Technol., 28, 25 (1995).
M. Wang, Y. Shao, J. Li, N. Zhu, M. Rangarajan, E. LaVoie, and Chi-T. Ho, J. Nat. Prod., 62, 454 (1999).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tirzite, D., Krauze, A., Zubareva, A. et al. Synthesis and Antiradical Activity of 5-Acetyl-2-alkylthio-4-aryl-6-methyl-1,4-dihydropyridine-3-carboxylic Acid Nitriles. Chemistry of Heterocyclic Compounds 38, 795–800 (2002). https://doi.org/10.1023/A:1020625519073
Issue Date:
DOI: https://doi.org/10.1023/A:1020625519073