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

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 (CO δ− --NH δ+ ), 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.