Synthesis, structural characterization, in silico ADMET and molecular docking studies of a Schiff base derived from 4-hydroxybenzaldehyde and 4-aminobenzoic acid

Abstract

The hemihydrate of the Schiff base derived from 4-hydroxybenzaldehyde and 4-aminobenzoic acid was synthesized and characterized using TG, ATR-FTIR, and SCXRD methods. Thermal analysis shows that the dehydration of 4-{(E)-[(4-hydroxyphenyl)methylidene]amino}benzoic acid hemihydrate occurs around 150 °C and yields a non-crystalline anhydrous form (m.p. = 241 °C). ATR-FTIR studies confirm the presence of an azomethine group (–HCN–). SCXRD experiments revealed that the title compound crystallizes in the monoclinic P2₁/n space group with two 4-(4-hydroxybenzylidene)aminobenzoic acid molecules and one water molecule in the asymmetric unit. In the crystal of the title compound, the Schiff base molecules are linked via O–H⋯O, O–H⋯N, and C–H⋯O hydrogen bonds, and C–H⋯π and π–π interactions. ADMET analysis indicates the synthesized compound's potential as a promising agent with high gastrointestinal absorption and the ability to cross the blood–brain barrier. Molecular docking studies predict its binding to the active sites of AChE and CA II.