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Synthesis, Crystal Structure, and Biological Activity of cistrans Amide Rotomers of (Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide
Joint Authors
Ghabbour, Hazem A.
Qabeel, Maha M.
Eldehna, Wagdy M.
Fun, Hoong-Kun
Abdel-Aziz, Hatem A.
Source
Issue
Vol. 2014, Issue 2014 (31 Dec. 2014), pp.1-7, 7 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2014-09-03
Country of Publication
Egypt
No. of Pages
7
Main Subjects
Abstract 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.
American Psychological Association (APA)
Abdel-Aziz, Hatem A.& Ghabbour, Hazem A.& Eldehna, Wagdy M.& Qabeel, Maha M.& Fun, Hoong-Kun. 2014. Synthesis, Crystal Structure, and Biological Activity of cistrans Amide Rotomers of (Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide. Journal of Chemistry،Vol. 2014, no. 2014, pp.1-7.
https://search.emarefa.net/detail/BIM-1040071
Modern Language Association (MLA)
Abdel-Aziz, Hatem A.…[et al.]. Synthesis, Crystal Structure, and Biological Activity of cistrans Amide Rotomers of (Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide. Journal of Chemistry No. 2014 (2014), pp.1-7.
https://search.emarefa.net/detail/BIM-1040071
American Medical Association (AMA)
Abdel-Aziz, Hatem A.& Ghabbour, Hazem A.& Eldehna, Wagdy M.& Qabeel, Maha M.& Fun, Hoong-Kun. Synthesis, Crystal Structure, and Biological Activity of cistrans Amide Rotomers of (Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide. Journal of Chemistry. 2014. Vol. 2014, no. 2014, pp.1-7.
https://search.emarefa.net/detail/BIM-1040071
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1040071