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

الملخص EN

(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.