Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline

  • Tamara Mijatović Innovation Center of the Faculty of Mechanical Engineering, University of Belgrade, Kraljice Marije 16,, 11000 Belgrade, Serbia
  • Milica Peric Innovation Center of the Faculty of Mechanical Engineering, University of Belgrade, Kraljice Marije 16,, 11000 Belgrade, Serbia
  • Luka Matović Innovation Center of the Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia
  • Marija Ristović Innovation Center of the Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia
  • Saša Drmanić Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

Abstract

Six ester and amide derivates of 2,6-dimethyl-4-(substituted)-1,4-dihydropyridine-3,5-dicarboxylic acid have been synthesized in this paper, including: diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(2-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, diethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. Obtained ester derivates were used afterwards as a starting compounds for synthesis of amide derivates, including: 2,6-dimethyl-4-phenyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6-dimethyl-4-(3-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 2,6-dimethyl-4-(4-nitrophenyl)-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(2-hydroxyphenyl)-2,6-dimethyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide, 4-(3-hydroxyphenyl)-2,6-dimethyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide and 4-(4-hydroxyphenyl)-2,6-dimethyl-N3,N5-di(thiazol-2-yl)-1,4-dihydropyridine-3,5-dicarboxamide. Obtained compounds were characterized by melting point, elementary analysis and FT-IR spectroscopy. In order to determine the effect of the substituent, the antioxidative activity assay of obtained 1,4-dihydropyridines was performed by using the DPPH (1,1-diphenyl-2-picryl-hydrazyl) free radical scavenging method.


Keywords: 1,4-dihydropyridines, esters, amides, antioxidative activity, DPPH, free radicals

Downloads

Download data is not yet available.

References

  • Ahamed A., Arif I. A., Mateen M., Kumar S. R. & A. Idhayadhulla A. (2018), Antimicrobial, anticoagulant, and cytotoxic evaluation of multidrug resistance of new 1,4-dihydropyridine derivatives. Saudi J. Biol. Sci., 25(6), 1227-1235. https://doi.org/10.1016/j.sjbs.2018.03.001

  • Datar P. A. & Auti P. B. (2016), Design and synthesis of novel 4-substituted 1,4-dihidropyridine derivates as hypotesive agents. Journal of Saudi Chemical Society, 20(5),510-516. https://doi.org/10.1016/j.jscs.2012.08.003

  • Debache A., Ghalem W., Boulcina R., Belfaitah A., Rhouati S. & Carboni B. (2009), An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component Hantzsch reaction under mild conditions. Tetrahedron Lett., 50(37), 5248–5250. https://doi.org/10.1016/j.tetlet.2009.07.018

  • Garcia E. J., Oldoni T. L. C., Alencar S. M., Reis A., Loguercio A. D. & Grande R. H. M. (2012), Antioxidant Activity by DPPH Assay of Potential Solutions to be Applied on Bleached Teeth. Braz Dent J. 23(1). https://doi.org/10.1590/S010364402012000100004 

  • Godfraind, T. (2005), Antioxidant effects and the therapeutic mode of action of calcium channel blockers in hypertension and atherosclerosis. Trans. R. Soc. B Biol. Sci., 360(1464), 2259–2272. https://doi.org/10.1098/rstb.2005.1774

  • Gullapalli, S. & Ramarao, P. (2002), L-type Ca2+ channel modulation by dihydropyridines potentiates kappa-opioid receptor agonist induced acute analgesia and inhibits development of tolerance in rats. Neuropharmacology 42(4), 467–475. https://doi.org/10.1016/S00283908(01)00200-3

  • Kumar A., Maurya R. A., Sharma S., Kumar M. & Bhatia G. (2010), Synthesis and biological evaluation of N-aryl-1,4-dihydropyridines as novel antidyslipidemic and antioxidant agents. J. Med. Chem., 45(2), 501–509. https://doi.org/10.1016/j.ejmech.2009.10.036

  • Love B., Goodman M., Snader K., Tedeschi R. & Macko E. (1974), Hantzsch-type dihydropyridine hypertensive agent. Med. Chem. 17(9), 956–965. https://doi.org/10.1021/jm00255a010

  • Mutha M., Antre R., Baheti K. & More P. (2013), study of Structure Based Drug Design for 1,4-Dihydropyridine derivates as Cox-II Inhibitors. Biol.Sci 13(6), 545-549. https://doi.org/10.3923/jbs.2013

  • Okoh S. O., Asekun O. T., Familioni O. B. & Afolayan A. J (2014), Antioxidant and Free Radical Scavenging Capacity of Seed and Shell Essential Oils Ectracted from Abrus precatorius (L), Antioxidants, 3(2), 278-287. https://doi.org/10.3390/antox3020278

  • Sunkel C. E., Juana M. F. & Santos L. (1990), 4-alkyl-1,4-dihydropyridines as specific PAF-acether antagonists. Med. Chem. 33(12), 3205–3210. https://doi.org/10.1021/jm00174a017

  • Tirzitis G., Tiryite D. & Hyvonen Z. (2001), Antioxidant activity of 2,6-dimethyl- 3,5-diethoxycarbonyl-1,4-dihydropyridines in Metal-Ion Catalyzed Lipid Peroxidation. Sci, Czech J Food, 19(3), pp. 81–84. https://doi.org/10.17221/6581-CJFS

  • Tirzite D., Krauze A., Zubareva A., Tirzitis G. & Duburs G. (2002), Synthesis and antiradical activity of 5-acetyl-2-alkylthio-4-aryl-6-methyl-1,4-dihydropyridine-3-carboxylic acid nitriles. Heterocycl. Compd. 38(7), 795–800. https://doi.org/10.1023/A:1020625519073

  • Zheleva-Dimitrova D., Nedialkov P. & Kitanov G. (2010), Radical scavenging and antioxidant activities of methanolic extract from Hypericum species growing in Bulgaria. Pharmacognosy magazine, 6(22), 74-78. https://doi.org/10.4103/0973-1296.62889
  • Published
    2018-12-31
    How to Cite
    MIJATOVIĆ, Tamara et al. Sinteza, karakterizacija i ispitivanje antioksidativne aktivnosti estarskih i amidnih derivata 2,6-dimetil-4-supstituisane-1,4-dihidropiridin-3,5-dikarboksilne kiseline. Journal of Engineering & Processing Management, [S.l.], v. 10, n. 2, p. 8-15, dec. 2018. ISSN 2566-3615. Available at: <https://jepm.tfzv.ues.rs.ba/index.php/Journal/article/view/194>. Date accessed: 20 may 2019. doi: https://doi.org/10.7251/JEPM181002008M.