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Synthesis, characterization, POM analysis and antifungal activity of novel heterocyclic chalcone derivatives containing acylated pyrazole

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Abstract

A series of heterocyclic chalcone derivatives (4a–h) were synthesized and characterized by IR, 1H and 13C NMR as well as MS. All the synthesized compounds were evaluated for their antifungal activity on Candida albicans and Aspergillus niger. The assay revealed that compounds 3d and 4f showed significant activity against both tested fungal strains. POM analyses showed that the compounds are highly lipophyllic but present a potential bioactivity. Moreover, they have no NH–O or N–HO intramoleculcular interaction which is a crucial parameter controlling solubility of compounds possessing these encouraging pharmaceutical properties. This series gives us an important lesson in drug design: We should take the balance of hydrosolubility/lipophilicity into consideration. POM analyses were in agreement with the idea of coexistence of two combined antifungal N,O and O,S-pharmacophore sites for series 4a–h. On the other hand, two coexistents and identical N,Cl-pharmacophore sites have been identified for Fluconazole.

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Acknowledgments

The authors wish to thank the Ministry of Higher Education (MOHE) for funding this research under the Research University Grant (RUP) with vote no 05H95 and Fundamental Research Grant Scheme (FRGS) of vote numbers 4F448. T.B.H. and Y.N.M. would like to extend their sincere appreciation to the Deanship of Scientific Research at king Saud University for funding this Research group No (PRG-1437-29).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310, Skudai, Johor, Malaysia

    Helmi Mohammed Al-Maqtari, Joazaizulfazli Jamalis, Noor Aisyah Ahmad & Hasnah Mohd Sirat

  2. LCM Laboratory, FSO, University of Mohammed Premier, Oujda, 60000, Morocco

    Taibi Ben Hadda

  3. Medicinal Chemistry Research Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Rajasthan, 333031, India

    Murugesan Sankaranarayanan & Subhash Chander

  4. Chemistry Department, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi Arabia

    Ismail I. Althagafi

  5. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia

    Yahia Naseer Mabkhot

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  1. Helmi Mohammed Al-Maqtari
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  2. Joazaizulfazli Jamalis
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  3. Taibi Ben Hadda
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  4. Murugesan Sankaranarayanan
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  5. Subhash Chander
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  6. Noor Aisyah Ahmad
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  7. Hasnah Mohd Sirat
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  8. Ismail I. Althagafi
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  9. Yahia Naseer Mabkhot
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Correspondence to Joazaizulfazli Jamalis or Taibi Ben Hadda.

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Al-Maqtari, H.M., Jamalis, J., Hadda, T.B. et al. Synthesis, characterization, POM analysis and antifungal activity of novel heterocyclic chalcone derivatives containing acylated pyrazole. Res Chem Intermed 43, 1893–1907 (2017). https://doi.org/10.1007/s11164-016-2737-y

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  • DOI: https://doi.org/10.1007/s11164-016-2737-y

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