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

• Main Authors: Hatem A. Abdel-Aziz, Hazem A. Ghabbour, Wagdy M. Eldehna, Maha M. Qabeel, Hoong-Kun Fun
• Format: Article
• Language: English
• Published: Hindawi Limited 2014-01-01
• Series: Journal of Chemistry
• Online Access: http://dx.doi.org/10.1155/2014/760434

(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-d6 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 a=4.5206 (1) Å, b=22.4747 (7) Å, c=17.3637 (5) Å, β=103.752 (1)°, Z=8, V=1713.57 (8) Å3, Dc=1.467 Mg m−3, μ=0.11 mm−1, F(000)=784, R=0.047, and wR=0.123 for 3798 observed reflections with I>2σ(I). 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.