Anthraquinonylhydrazones of α-Active Ketones and β-Carbonyl-containing Compunds: Synthesis and Antioxidant Activity

Nazar Kopak1
Maryna Stasevych1 maryna.v.stasevych [at] gmail.com
Viktor Zvarych1
Nahide Gulsah Deniz2 yurdakul [at] istanbul.edu.tr
Cigdem Sayil2
Mustafa Ozyurek3 mozyurek [at] istanbul.edu.tr
Kubilya Guclu3
Mykhailo Vovk4 mvovk [at] ioch.kiev.ua
Volodymyr Novikov1
  1. Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Ukraine, Lviv, S. Bandery street 12
  2. Division of Organic Chemistry, Istanbul University, Turkey, Istanbul, 34320, Avcilar
  3. Department of Chemistry, Division of Analytical Chemistry, Turkey, Istanbul, 34320, Avcilar
  4. Department ofMechanisms of Organic Reactions, Ukraune, Kyiv, Murmanska Str. 5,
Abstract 

An effective method for the synthesis of 1-anthraquinonyl hydrazones containing the acyl- and/or ethoxycarbonyl, carbo- and heterocyclic fragments in the ylidene moiety has been shown, which are convenient reagents for further chemical transformations. Investigation of the antioxidant activity of hydrazones has allowed to identify promising compounds that can be suggested for further research as antioxidant substances.

References 

[1] N. Belskaya, W. Dehaen, V. Bakulev, “Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions,” Arkivoc, vol. I, pp. 275-332, 2010.

[2] R. Ali, A. Marella, T. Alam, R. Naz, M. Akhter, Md. Shaquiquzzaman, R. Saha, O. Tanwar, M. Alam, J. Hooda, “Review of biological activities of hydrazones,” Indones. J. Pharm., vol. 23, pp. 193-202, 2012.

[3] Q.A. Acton, Ed., Anthraquinones. Advances in Research and Application. Atlanta : Scholarly Editions, 2013.

[4] S. Arai, S. Kato, M.B. Hida, “Anthraquinone pharmaceutical compounds and uses therefor,” J. Chem. Soc. Jpn., vol. 58, p. 1458, 1985.

[5] I. Antonini, P. Polucci, D. Cola, G. Palmieri, S. Martelli, M. Bon-temps-Gracz, “Synthesis of 9,10-anthraquinone monoalkylaminoalkylhydrazones as potential antitumor drugs,” Farmaco, vol. 48, pp. 1641 1648, 1993.

[6] V.A. Loskutov, “Reaction of anthrone and its 1-and 4-substituted derivatives with sulfur in the presence of nucleophiles,” Russ. J. Org. Chem., vol. 36, pp. 1478- 1481, 2000.

[7] M. Regitz, “Reaktionen aktiver Methylen-verbindungen mit Aziden, III. Über die Diazo-, Azino- und Triphenylphosphazino-Derivate des Anthrons und Thioxanthen-S-dioxids,” Chem. Ber., vol. 97, pp. 2742- 2754, 1964.

[8] S.L. Vorob’eva, V.N. Buyanov, I.I. Levina, N.N. Suvorov, “Naphthindoles. 2. Naphtho[2,3-e]indole-4,9- diones and naphtho[2,3-f]indole-5,10-diones,” Chem. Heterocycl. Compd., vol. 25, pp. 646–649, 1989.

[9] K. MeeKyoung, D.F. Wiemer, “EDC-mediated condensations of 1-chloro-5-hydrazino-9, 10-anthracenedione, 1-hydrazino-9,10-anthracenedione, and the corresponding anthrapyrazoles,” Tetrahedron Lett., vol. 45, pp. 4977- 4980, 2004.

[10] V. Zvarych, M. Stasevych, V. Lunin, N.G. Deniz, C. Sayil, M. Ozyurek, K. Guclu, M. Vovk, V. Novikov, “Synthesis and investigation of antioxidant activity of the dithiocarbamate derivatives of 9,10 anthracenedione”, Monatsh. Chem., vol. 147, pp. 2093-2101, 2016.

[11] R. Apak, K. Güçlü, M. Özyürek, S.E. Karademir, “Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method,” J. Agric. Food Chem., vol.52, pp.7970-7981, 2004.

[12] B. Bekdeşer, M. Özyürek, K. Güçlü, F. Üstün Alkan, R. Apak,“Development of a new catalase activity assay for biological samples using optical CUPRAC sensor,” Spectrochim. Acta Part A, vol. 132, pp. 485 490, 2014.