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Journal of Chemistry
Volume 2014, Article ID 760434, 7 pages
http://dx.doi.org/10.1155/2014/760434
Research Article

Synthesis, Crystal Structure, and Biological Activity of cis/trans Amide Rotomers of (Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide

1Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
2Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt
3Department of Pharmaceutical Chemistry, College of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt
4Department of Clinical Microbiology and Immunology, College of Medicine, Mansoura University, Mansoura 35516, Egypt
5X-Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia (USM), 11800 Penang, Malaysia

Received 29 May 2014; Revised 26 July 2014; Accepted 12 August 2014; Published 3 September 2014

Academic Editor: Nigam P. Rath

Copyright © 2014 Hatem A. Abdel-Aziz 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

(Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide (2) was synthesized by the reaction of (Z)-3-hydrazonoindolin-2-one (1) with formic acid under reflux. The structure of 2 was characterized by IR, Mass, 1H NMR, and X-ray crystal structure determination. Interestingly, compound 2 appeared in DMSO- as cis and trans amide rotomers in 25% and 75%, respectively. The X-ray analysis showed the Z geometrical isomer of 2 around –C=N– for cis and trans amide rotomers. The crystal of 2 belongs to monoclinic, space group P21/c, with (1) Å, (7) Å, (5) Å, (1)°, , (8) Å3,  Mg m−3,  mm−1, , , and for 3798 observed reflections with . Compound 2 exhibited a moderate activity in its antimicrobial evaluation against E. coli and P. aeruginosa and a good activity against S. aureus close to that of the standard drug ciprofloxacin. The in vitro anticancer activity of 2 was evaluated against two human tumor cell lines, namely, HepG2 hepatocellular carcinoma and MCF-7 breast cancer. HepG2 cancer cell line was more susceptible to compound 2 than MCF-7.