Structure and POM analyses of 2-{(2Z)-2-[(2R)-2-ethoxy-4-oxo-2H-chromen-3(4H)-ylidene]hydrazinyl}benzonitrile with promising parasitological activity

Structure and POM analyses of... Functionalised chromanone (4) is prepared by the condensation of aryldiazonium salt (2) and enaminones (1) in ethanol at room temperature. The structure of (4) was determined by spectral (IR, 1H and 13C NMR), elemental and X-ray diffraction analysis. Compound 4 (C18H15N3O3) crystallizes in the monoclinic space group P21/c with a = 7.9182(5), b = 21.729(2), c = 9.6217(7) Å, β = 97.293(6)°, V = 1642.0(2) Å3, Z = 4. The molecule of compound (4) is bent at the C-16 atom with a C15–O2–C16–C8 torsion angle of 46.18(3)°. Intramolecular phenolic N–H···O hydrogen bonds are also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 4.488(12) Å. The preliminary POM analyses of 4 confirm the coexistence of two combined antibacterial and antiparasite pharmacophore sites. Therefore, compound 4 is promising and it should be screened without hesitation against virulent and pathogenic biotargets. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Structure and POM analyses of 2-{(2Z)-2-[(2R)-2-ethoxy-4-oxo-2H-chromen-3(4H)-ylidene]hydrazinyl}benzonitrile with promising parasitological activity

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Publisher
Springer Netherlands
Copyright
Copyright © 2015 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-015-2143-x
Publisher site
See Article on Publisher Site

Abstract

Functionalised chromanone (4) is prepared by the condensation of aryldiazonium salt (2) and enaminones (1) in ethanol at room temperature. The structure of (4) was determined by spectral (IR, 1H and 13C NMR), elemental and X-ray diffraction analysis. Compound 4 (C18H15N3O3) crystallizes in the monoclinic space group P21/c with a = 7.9182(5), b = 21.729(2), c = 9.6217(7) Å, β = 97.293(6)°, V = 1642.0(2) Å3, Z = 4. The molecule of compound (4) is bent at the C-16 atom with a C15–O2–C16–C8 torsion angle of 46.18(3)°. Intramolecular phenolic N–H···O hydrogen bonds are also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 4.488(12) Å. The preliminary POM analyses of 4 confirm the coexistence of two combined antibacterial and antiparasite pharmacophore sites. Therefore, compound 4 is promising and it should be screened without hesitation against virulent and pathogenic biotargets.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jul 9, 2015

References

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