Synthesis, Structural Characterization, and In Silico Evaluation of the Salicylidene Schiff Base 4‑{(E)‑[(2,3-Dihydroxyphenyl)methylidene]amino}-2-hydroxybenzoic Acid as a Promising Scaffold for Human Transthyretin Inhibitor

The Schiff base derived from the condensation of 4-aminosalicylic
acid with 2,3-dihydroxybenzaldehyde was synthesized and characterized
by using experimental techniques, theoretical calculations, and in
silico methods. Single-crystal X-ray diffraction analysis showed that
the compound crystallizes in the triclinic P1̅
space group with two molecules in the asymmetric unit, both adopting
a zwitterionic keto form. In silico studies predict high gastrointestinal
absorption, low toxicity, and potential activity as a transthyretin
(TTR) inhibitor, with binding affinity comparable to that of the drug
Tolcapone, suggesting that the synthesized compound may be a promising
scaffold for a TTR stabilizer.