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Vol. 26 No. 23 (2014)

Copyright (c) 2014 Wei-Ming Zhang1, Gui-Hua Sheng2, Zhonglu You3

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This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Crystal Structures and Xanthine Oxidase Inhibitory Activity of Benzohydrazone Compounds

https://doi.org/10.14233/ajchem.2014.17602
Wei-Ming Zhang1
1Nanjing Institute for the Comprehensive Utilization of Wild Plant, Nanjing 210042, P.R. China 2School of Life Sciences, Shandong University of Technology, Zibo 255049, P.R. China 3Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P.R. China *Corresponding author: E-mail: youzhonglu@126.com
Gui-Hua Sheng2
1Nanjing Institute for the Comprehensive Utilization of Wild Plant, Nanjing 210042, P.R. China 2School of Life Sciences, Shandong University of Technology, Zibo 255049, P.R. China 3Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P.R. China *Corresponding author: E-mail: youzhonglu@126.com
Zhonglu You3
1Nanjing Institute for the Comprehensive Utilization of Wild Plant, Nanjing 210042, P.R. China 2School of Life Sciences, Shandong University of Technology, Zibo 255049, P.R. China 3Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P.R. China *Corresponding author: E-mail: youzhonglu@126.com

Corresponding Author(s) : Wei-Ming Zhang1

Asian Journal of Chemistry, Vol. 26 No. 23 (2014)

Abstract

A series of three benzohydrazone compounds, 2N'-(5-hydroxy-2-nitrobenzylidene)-4- methylbenzohydrazide (1), N'-(5-chloro-2-hydroxybenzylidene)-3-methylbenzohydrazide (2) and N'-(2,4-dichlorobenzylidene)-3-methylbenzohydrazide (3), were prepared and structurally characterized by elemental analysis, IR spectra and single crystal X-ray determination. Xanthine oxidase inhibitory activities of the compounds were studied. Among the compounds, N'-(5-hydroxy-2-nitrobenzylidene)-4-methylbenzohydrazide (1) shows the most effective activity with IC50 value of 15.2 ± 2.3 μM. Docking simulation was performed to insert the compound into the crystal structure of xanthine oxidase at the active site to investigate the probable binding modes.

Keywords

Benzohydrazone Xanthine oxidase Inhibition Crystal structure Molecular docking study.
Zhang1, W.-M., Sheng2, G.-H., & You3, Z. (2014). Synthesis, Crystal Structures and Xanthine Oxidase Inhibitory Activity of Benzohydrazone Compounds. Asian Journal of Chemistry, 26(23), 8118–8122. https://doi.org/10.14233/ajchem.2014.17602
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References
  1. D.W. Banner and P. Hadvary, J. Biol. Chem., 266, 20085 (1991).
  2. E. Sandstrom, Drugs, 38, 417 (1989).
  3. P.H. Chan, J.W. Schmidley, R.A. Fishman and S.M. Longar, Neurology, 34, 315 (1984).
  4. H.S.D. Naeff, M.C.R. Franssen and H.C. van der Plas, Recl. Trav. Pay-B, 110, 139 (1991).
  5. P. Pacher, A. Nivorozhkin and C. Szabo, Pharmacol. Rev., 58, 87 (2006).
  6. A.A. Fatokun, T.W. Stone and R.A. Smith, Neurosci. Lett., 416, 34 (2007).
  7. R.K. Robins, G.R. Revankar, D.E. O'Brien, R.H. Springer, T.N.A. Albert, K. Senga, J.P. Miller and D.G. Streeter, J. Heterocycl. Chem., 22, 601 (1985).
  8. K. Okamoto, B.T. Eger, T. Nishino, E.F. Pai and T. Nishino, Nucleos. Nucleot. Nucl. Acids, 27, 888 (2008).
  9. A. Haberland, H. Luther and I. Schimke, Agents Actions, 32, 96 (1991).
  10. H.-J. Zhang, X. Qin, K. Liu, D.-D. Zhu, X.-M. Wang and H.-L. Zhu, Bioorg. Med. Chem., 19, 5708 (2011).
  11. M.S. Alam, J.H. Choi and D.U. Lee, Bioorg. Med. Chem., 20, 4103 (2012).
  12. K. Cheng, Q.-Z. Zheng, Y. Qian, L. Shi, J. Zhao and H.-L. Zhu, Bioorg. Med. Chem., 17, 7861 (2009).
  13. M. Leigh, C.E. Castillo, D.J. Raines and A.K. Duhme-Klair, Chem. Med. Chem., 6, 612 (2011).
  14. L.D. Kong, Y. Cai, W.W. Huang, C.H.K. Cheng and R.X. Tan, J. Ethnopharmacol., 73, 199 (2000).
  15. Bruker, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA (2002).
  16. G.M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector, University of Göttingen, Germany (1996).
  17. G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008).
  18. Y. Lu, D.-H. Shi, Z.-L. You, X.-S. Zhou and K. Li, J. Coord. Chem., 65, 339 (2012).
  19. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987).
  20. M. Zhang, D.-M. Xian, H.-H. Li, J.-C. Zhang and Z.-L. You, Aust. J. Chem., 65, 343 (2012).
  21. S. Gupta, L.M. Rodrigues, A.P. Esteves, A.M.F. Oliveira-Campos, M.S.J. Nascimento, N. Nazareth, H. Cidade, M.P. Neves, E. Fernandes and M. Pinto, Eur. J. Med. Chem., 43, 771 (2008).
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