Synthesis, Computational Studies, Molecular Docking, Anti-inflammatory and Antioxidant Activities of alpha-Aminophosphonates Incorporating an Azo Chromophore for Polyester Printing Application

Bioisosteres of amino acids called a-aminophosphonates have a variety of therapeutic properties. A set of procedures involving amine, aldehydes and triethylphosphite have been utilized to synthesize these compounds in presence of Lewis acid catalysts such as lithium perchlorate via the Kabachnik-Fields reaction. The diazonium salt of different aromatic amines affords new a-aminophosphonate azo dyes, IIIa-f in high yields. The structure of the newly synthesized compounds was elucidated by FT-IR, (HNMR)-H-1, C-13-NMR and elemental analysis. The anti-inflammatory and antioxidant of the newly dyes was also examined. Most of the synthesized a-aminophosphonate compounds displayed an excellent to moderate activity against COX-1 and COX-2. To demonstrate the relationship between the theoretical and the experimental characteristics, DFT/6-311G++(d, p) calculations were performed to investigate the electrical and geometric properties derived from the stable structure of the compounds. The optimized dyes with printing paste conditions, were used to silk screen printing polyester, as well as their printing properties, light, washing, perspiration, rubbing, and sublimation fastness were tested. Meanwhile, the improved dyes demonstrated acceptable fastness results.