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

How to improve antifungal bioactivity: POM and DFT study of some chiral amides derivatives of... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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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Publisher
Springer Journals
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2578-8
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: May 20, 2016

References

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