How to improve antifungal bioactivity: POM and DFT study of some chiral amides derivatives of diacetyl-L- tartaric acid and amines Yahia N. Mabkhot 1 • Muhammad Arfan 2 • Hsaine Zgou 3 • Zuhal K. Genc 4 • Murat Genc 5 • Abdur Rauf 6 • Saud Bawazeer 7 • Taibi Ben Hadda 8 Received: 14 January 2016 / Accepted: 10 May 2016 Ó Springer Science+Business Media Dordrecht 2016 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 pharma- cophore sites. The six compounds 4–9 analyzed here were previously experimen- tally 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 d- –NH d? ), which plays a crucial template role in the organization of antifungal O,O-phramacophore sites. Moreover, it is cheap, has fewer side effects, & Taibi Ben Hadda taibi.ben.hadda@gmail.com 1 Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia 2 Department of Chemistry, School of Natural Sciences (SNS), National University of Sciences and Technology (NUST), H-12, Islamabad, Pakistan 3 Polydisciplinary Faculty, Ibn Zohr University, Ouarzazate 45000, Morocco 4 Department of Metallurgy and Materials Engineering, Faculty of Engineering, Adiyaman University, 02040 Adiyaman, Turkey 5 Department of Chemistry, Faculty of Science and Arts, Adiyaman University, 02040 Adiyaman, Turkey 6 Department of Geology, University of Swabi, Anbar, Khyber Pakhtunkhwa 23561, Pakistan 7 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, P. O. Box 42, Makkah, Saudi Arabia 8 LCM Laboratory, Faculty of Sciences, University of Mohammed 1st, 60000 Oujda, Morocco 123 Res Chem Intermed DOI 10.1007/s11164-016-2578-8