SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of <i>α‐</i>aminophosphonates, DFT calculations and, computer aided design in antifungal activity

Abstract

Abstract SB‐2 cationic resin has been employed as an unexpected and reusable heterogeneous organocatalyst in multicomponents reaction for the synthesis of the α‐ aminophosphonates derivatives that act as antifungal agents, this reaction proceeds under eco‐friendly and simple procedure by condensation in one pot of substituted aromatic aldehydes, anilines and diethylphosphite. Excellent isolated product yields are obtained (up to 70 %) for ( 4 a – o ) within shorter reaction times in solvent‐free condition. The synthesized compounds were determined by spectroscopic analyses such as: NMR ( 1 H, 13 C and 31 P), IR and HRMS.Molecular geometries, electronic properties, stability and reactivity such as: HOMO/LUMO, , dipole moment (6.1308&lt; D &lt;10.5829), electronegativity (2.3490&lt; X &lt;3.5892), electrophilicity (1.1046&lt; ω &lt;3.2185) and the calculated thermodynamic descriptors (Zero‐point Energies, Enthalpy and Gibbs Free Energy) of four trimethoxy α‐ aminophosphonates derivatives ( 4 j , 4 k , 4 l and 4 m ) were carried by DFT at B3LYP 6‐31G (d, p) basis set. Computer aided design by molecular docking of studied compounds revealed a good binding energy against 5HS1 receptor to be considered as antifungal candidates and compared with Voriconazole. In additionally, druglikeness parameters of selected compounds were found through in silico pharmacological ADME/T properties estimation.