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

• Five new 10-heterylazo-9-anthrone derivatives were synthesised and characterized. • The solvatochromic property of reported compounds is produced by the formation of H-bond complexes with solvents. • Based on molecular docking modelling, the pharmacokinetics and anticancer activity were evaluated for pancreatic cancer. • In vitro antibacterial activity was evaluated for the five anthrone derivatives with compound I described as the most active. • Compound III and IV presented a promising efficacy in combating pancreatic carcinoma. In this paper, a new series of five promising 10-heterylazo-anthracen-9(10 H)-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, 1H- and 13C-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. Synthesis of new anthrone derivatives and their azo-hydrazone tautomeric forms. Image, graphical abstract [ABSTRACT FROM AUTHOR]