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Journal of Chemistry
Volume 2014, Article ID 154357, 8 pages
http://dx.doi.org/10.1155/2014/154357
Research Article

Design, Synthesis, and Molecular Docking of 1-(1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine as Potent Nonazole Anticandidal Agent

1Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
2Department of Clinical Microbiology and Immunology, College of Medicine, Mansoura University, Mansoura 35516, Egypt
3Department of Pharmaceutical Chemistry, College of Pharmacy, Egyptian Russian University, P.O. Box 11829, Badr City, Cairo, Egypt
4Stem Cell and Tissue Re-Engineering Program, Research Center, King Faisal Specialist Hospital and Research Center, P.O. Box 3354, MBC 03, Riyadh 11211, Saudi Arabia
5Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt

Received 18 October 2014; Revised 14 December 2014; Accepted 14 December 2014; Published 31 December 2014

Academic Editor: Tanaji Talele

Copyright © 2014 Hazem A. Ghabbour et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

1-(1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine (13) was designed and synthesized as potential nonazole anticandidal agent and precisely characterized by IR, 1H NMR, 13C NMR, and ESI-MS. The anti-Candida activity of 13 was evaluated against four Candida species (C. albicans, C. krusei, C. parapsilosis, and C. glabrata). Compound 13 displayed good anticandidal activities (, 0.195, 0.39, and 1.56 μmol/mL, resp.) in comparison with that of the standard drug fluconazole (, inactive, 1.56, and 1.56 μmol/mL, resp.) against C. albicans, C. krusei, C. parapsilosis, and C. glabrata, respectively. A molecular modeling of the newly synthesized compound 13 was built in order to investigate its mode of action towards the prospective target cytochrome P450-dependent enzyme lanosterol 14α-demethylase (PDB-code: 1EA1). The docking results showed a similar binding interaction of 13 and fluconazole at the active site of CYT P450 14α-sterol demethylase. Furthermore, compound 13 showed no cytotoxicity against normal human breast cell line MCF10A.