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

(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- d 6 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 p2c,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,d c = 1.467 mg m-3,= 0.11 mm-1,f (000) = 784,r = 0.047,and w r = 0.123 for 3798 observed reflections with i > 2 σ (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. © 2014 hatem a. abdel-aziz et al.