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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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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.

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Acknowledgments

We gratefully acknowledge the Department of Chemistry, Sciences Faculty for Girls at the King Abdulaziz University in Jeddah, Kingdom of Saudi Arabia for their support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Sciences Faculty for Girls, King Abdulaziz University, P.O. Box 50918, Jeddah, 21533, Kingdom of Saudi Arabia

    Khadijah Al-Zaydi

  2. Department of Chemistry, King Saud University, P.O. Box 2455, Riyadh, 11451, Kingdom of Saudi Arabia

    Saad M. Alshehri

  3. Materials Chemistry Laboratory, Faculty of Sciences, Mohammed First University, 60000, Oujda, Morocco

    Taibi Ben Hadda

Authors
  1. Khadijah Al-Zaydi
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  3. Taibi Ben Hadda
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Correspondence to Taibi Ben Hadda.

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Al-Zaydi, K., Alshehri, S.M. & Ben Hadda, T. Structure and POM analyses of 2-{(2Z)-2-[(2R)-2-ethoxy-4-oxo-2H-chromen-3(4H)-ylidene]hydrazinyl}benzonitrile with promising parasitological activity. Res Chem Intermed 42, 2201–2210 (2016). https://doi.org/10.1007/s11164-015-2143-x

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