Abstract
The method of Hantzsch was used to synthesize esters and amides of 2,6-dimethyl-4-aryl-1,4-dihydropyridine-3,5-dicarboxylic acid, containing electron donor substituents in the phenyl ring. It was found that in addition to their antioxidant properties, 3,5-diamides and 4-(3′,4′-dioxyphenyl) derivatives have an affinity for model phospholipid membranes.
Similar content being viewed by others
References
E. M. Marinova and N. V. Yanishlieva, Fat. Sci. Technol.,94, 428 (1992).
J. Lehuede, F. Huguet, B. Fauconneau, A. Piriou, and J. M. Vierfond, Eur. J. Med. Chem.,31, 71 (1996).
W. B. Weglicki, I. T. Mak, and M. G. Simic, J. Mol. Cellul. Cardiol.,22, 1199 (1990).
G. Ya. Dubur, Yu. A. Zilber, A. Kh. Velena, A. O. Kumerova, and G. D. Tirzit, Izv. Akad. Nauk LatvSSR, No. 7, 65 (1975).
G. Tirzitis, I. Kirule, and G. Duburs, Fat Sci. Technol.,90 411 (1988).
A. Kh. Velena, Author's abstract of dissertation for the degree of candidate of biological sciences, Riga (1975).
L. Kourimska, J. Pokorny, and G. Tirzitis, Nahrung,37, 91 (1993).
I. E. Kirule, Author's abstract of dissertation for the degree of candidate of chemical sciences, Riga (1987).
S. M. Jain, Kant Ravi, Devi Sunita, K. L. Dhar Singh Surjeet, S. Bani, and G. B. Singh, Indian J. Chem.,29B, 95 (1990).
Z. M. Yang and Y. M. Dong, Acta Pharm. Sinica,26, 661 (1991).
L. E. Hinkel and W. R. Mandel, J. Chem. Soc.,135, 750 (1929).
Pat. 531,033 Span. ES; M. J. Verde Casanove and G. A. Galiano Ramos, chem. Abstr.,105, 226361 (1986).
A. Philips, J. Am. Chem. Soc.,71, 4003 (1949).
Pat. 6,801,482 S. African; F. Bossert and W. Vater, Chem. Abstr.,70, 96641 (1967).
Pat. 1,294,650 UK; S. Giller, G. Dubur, Y. Yldrikis, G. Tirzit, A. Valdman, I. Zakharchenko, Y. Spruz, V. Ronis, and A. Makarov, Chem. Abstr.,78, 159440 (1979).
Pat. 1,521,913 UK; S. Giller, G. Dubur, G. Tirzitis, Y. Uldrikis, E. Kozlov, R. Ivanova, V. Yakovlek, N. Bogoslovsky, and Zh. Abramova, Chem. Abstr.,90, 136453 (1979).
G. Ya. Dubur, Z. Ya. Ogle, and Ya. R. Uldrikis, Khim. Geterotsikl. Soedin., No. 12, 1642 (1974.
R. Schiff and J. Puliti, Ber.,16, 1607 (1883).
H. E. Miller, J. Am. Oil Chem. Soc.,48, 91 (1971).
G. J. Marco, J. Am. Oil Chem. Soc.,45, 594 (1968).
I. Kirule, G. Tirzitis, and G. Duburs, LPSR ZA Vestis. Khim. Ser., No. 3, 354 (1990).
E. V. Ivanov, T. V. Ponomarjova, G. N. Merkusev, G. Ja. Dubur, E. A. Bisenieks, A. Z. Dauvarte, and E. M. Pilscik, Radiobiol. Radiother.,31, No. 1, 69 (1990).
N. V. Makarova, G. V. Belevich, E. A. Bisenieks, M. M. Veveris, and G. Ya. Dubur, Khim.-Farm. Zh., No. 7, 810 (1988).
N. V. Makarova, Zh. V. Koronova, A. V. Plotnietse, D. Ya. Tirzite, G. D. Tirzit, and G. Ya. Duburs, Khim. Geterotsikl. Soedin., No. 8, 1112 (1995).
F. T. Van Amsterdam, A. Roveri, M. Malorino, E. Ratti, and F. Ursini, Free Radic. Biol. Med.,12, 183 (1992).
R. P. Mason, D. G. Rhodes, and L. G. Herbette, J. Med. Chem.,34, 869 (1991).
J. S. Hinzmann, R. L. McKenna, T. S. Pierson, F. Han, F. J. Kezdy, and D. E. Epps, Chem. and Phys. Lipids,62, 123 (1992).
Additional information
Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp, 1358–1365, October, 1996. Original article submitted June 20, 1996.
Rights and permissions
About this article
Cite this article
Plotnietse, M., Tirzitis, G., Uldrikis, Y. et al. Synthesis of 1,4-dihydropyridine derivatives having an oxy-, alkoxy-, or dimethylaminophenyl substituent in the 4 position, their antioxidant activity, and their binding to phospholipid membranes. Chem Heterocycl Compd 32, 1166–1172 (1996). https://doi.org/10.1007/BF01169228
Issue Date:
DOI: https://doi.org/10.1007/BF01169228