Structural Characterization and pharmacokinetic profile of boronic acid-functionalized bis-Schiff base

A new bis-Schiff base molecule (E) derived from 1,5-diaminonaphthalene and 4-formylphenylboronic acid was synthesized via a condensation reaction and obtained in high yield. The molecular structure was unambiguously established by single-crystal X-ray diffraction analysis, revealing a centrosymmetric bis-imine framework crystallizing in the triclinic P-1 space group with DMF solvation. The azomethine (C=N) bond length confirms the formation of the imine linkage, while intermolecular O-H···O hydrogen bonds between boronic acid groups generate one-dimensional supramolecular chains in the solid state. The structure is further stabilized by CH···π and CH···O interactions. The compound was fully characterized by FT-IR and 1H/13C NMR spectroscopy and elemental analysis results were consistent with the calculated values. UV-Vis absorption and photoluminescence studies indicate the presence of an extended π-conjugated system. In silico pharmacokinetic evaluation using SwissADME suggests favorable drug-likeness, high predicted gastrointestinal absorption, and compliance with major drug-likeness rules. The combined structural, optical, and theoretical pharmacokinetic findings highlight the multifunctional potential of this boronic acid-functionalized Schiff base scaffold.