1-(3-Methylthiophene-2-yl)-N-(3,4,5-trimethoxyphenyl)methanimine: Synthesis, Spectroscopic Characterization, Antileishmanial Activity, and DFT and In Silico Studies

1-(3-Methylthiophen-2-yl)-N-(3,4,5-trimethoxyphenyl)methanimine (1, MTM) was synthesized from 3-methylthiophene-2-carbaldehyde and 3,4,5-trimethoxyaniline and characterized by FTIR and H-1 and C-13 NMR spectra. The geometric structure of the title compound was optimized, and its electronic (FMO, NLO, MEP, NBO), spectroscopic (NMR, IR, UV), and thermodynamic properties were calculated by quantum chemicial methods. The calculated and experimental geometric parameters were compared with each other. Compound 1 was tested for leishmanicidal activity against Leishmania infantum by the broth microdilution method and was found to be efficient against Leishmania infantum promastigotes in the concentration range studied. Possible interactions responsible for the antileishmanial activity were determined by molecular docking analysis against trypanothione reductase (TRe). The docking results demonstrated high inhibition constant of the title compound and supported its antileishmanial activity.