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How to improve antifungal bioactivity: POM and DFT study of some chiral amides derivatives of diacetyl-L-tartaric acid and amines

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Abstract

A computational Petra/Osiris/Molinspiration and Density Functional Theory based model has been developed for the identification of physic–chemical parameters governing the bioactivity of chiral amides derivatives of diacetyl-L-tartaric acid and aromatic amines 4–9 containing combined antifungal pharmacophore sites. The six compounds 4–9 analyzed here were previously experimentally and now virtually screened for their antibacterial/antifungal activity. The highest antifungal activity was obtained for compound 6, which exhibited excellent % inhibition, comparable to Terbinafine. Compound 5, represents increased activity as compared to its isomer 6. The increase of bioactivity from 5 to 6 could be attributed to the existence of pi-charge transfer from para-Bromo-phenyl to its amid group (COδ−--NHδ+), which plays a crucial template role in the organization of antifungal O,O-phramacophore sites. Moreover, it is cheap, has fewer side effects, and its possible inclusions in selective fungal/viral media such as Fusarium, HIV, and Hepatitis B/C have to be questioned.

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Acknowledgments

The authors greatly acknowledge the Higher Education Commission of Pakistan for funding this research. 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 its funding of this Research group N (PRG-1437-29).

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Authors and Affiliations

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

    Yahia N. Mabkhot

  2. Department of Chemistry, School of Natural Sciences (SNS), National University of Sciences and Technology (NUST), H-12, Islamabad, Pakistan

    Muhammad Arfan

  3. Polydisciplinary Faculty, Ibn Zohr University, Ouarzazate, 45000, Morocco

    Hsaine Zgou

  4. Department of Metallurgy and Materials Engineering, Faculty of Engineering, Adiyaman University, 02040, Adiyaman, Turkey

    Zuhal K. Genc

  5. Department of Chemistry, Faculty of Science and Arts, Adiyaman University, 02040, Adiyaman, Turkey

    Murat Genc

  6. Department of Geology, University of Swabi, Anbar, Khyber Pakhtunkhwa, 23561, Pakistan

    Abdur Rauf

  7. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, P. O. Box 42, Makkah, Saudi Arabia

    Saud Bawazeer

  8. LCM Laboratory, Faculty of Sciences, University of Mohammed 1st, 60000, Oujda, Morocco

    Taibi Ben Hadda

Authors
  1. Yahia N. Mabkhot
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  2. Muhammad Arfan
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  8. Taibi Ben Hadda
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Correspondence to Taibi Ben Hadda.

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Mabkhot, Y.N., Arfan, M., Zgou, H. et al. How to improve antifungal bioactivity: POM and DFT study of some chiral amides derivatives of diacetyl-L-tartaric acid and amines. Res Chem Intermed 42, 8055–8068 (2016). https://doi.org/10.1007/s11164-016-2578-8

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