Synthesis, characterization, PASS prediction, molecular docking and ADME study of benzo[b]thiophen-5-amine based biologically active Schiff bases

Abstract

Adopting the potentiality of benzo[b]thiophene moiety and Schiff base compounds, a series of Schiff base compounds namely, 2-{[(1-benzothiophen-5-yl)imino]methyl}phenol i.e. 5a, 3-{[(1-benzothiophen-5-yl)imino]methyl}benzene-1,2-diol i.e. 5b, 2-{[(1-benzothiophen-5-yl)imino]methyl}-6-methoxyphenol i.e. 5c, 2-{[(1-benzothiophen-5-yl)imino]methyl}-5- methoxyphenol i.e. 5d, 2-{[(1-benzothiophen-5-yl)imino]methyl}-4-nitrophenol i.e. 5e and 2-{[(1-benzothiophen-5- yl)imino]methyl}-4-chlorophenol i.e. 5f have been synthesized in good yields and characterized by FT-IR, 1H and 13C NMR, and mass spectroscopy. Biological activity has been checked after performing antimicrobial and antifungal activity studies of synthesized compounds using the Minimum Inhibitory Concentration (MIC) determination technique. Computational studies like PASS (Prediction of Activity Spectra for Substances) prediction, molecular docking, and an ADME (Absorption, Distribution, Metabolism, Excretion) study have been performed to gain insight into the synthesized molecules’ in silico properties.