Synthesis, spectroscopic and molecular docking studies of novel 10-heterylazo-9-anthrone derivatives as potential antimicrobial and anticancer agents

In this paper, a new series of five promising 10-heterylazo-anthracen-9(10H)-one derivatives (I-V) was synthesized and screened for their antimicrobial activities. The chemical and tautomeric structures of the newly synthesized compounds were confirmed by FT-IR, UV, H-1- and C-13-NMR spectroscopy. Spectral investigation confirms the presence of tautomerism only for compounds I, III and IV. The electronic spectra and solvatochromic behavior of these compounds were studied and the solvated H-bond complexes formed in solution were examined. Solvatochromic behaviour of these compounds was studied by observing changes in the electronic spectra in mixture of solvents with different polarity. From the results it is evident that solvatochromic effect is produced by the formation of H-bond complexes. Results of antimicrobial screening demonstrated that these new derivatives had a respectable antibacterial activity and compound I emerged as the most active. In addition, molecular docking studies of all compounds and their isomers were performed to predict their binding patterns towards the active Rab20 site that is found regulated in the human pancreatic tumor. The results would suggest that these compounds could bind to Rab20 effectively which could result in important biochemical modification and probably affecting the growth and survival. (C) 2020 Elsevier B.V. All rights reserved.