Synthesis, molecular structure and multiple biological activities of β-cycloketols using methylamine catalyst

Abstract

The reaction of substituted benzaldehyde with acetylacetone in the presence of methylamine as a catalyst leads to the formation of β-cycloketols were successfully synthesized and systematically characterized by using 1H NMR, 13C NMR and FT-IR spectroscopic techniques. For 2, HOMOCOSY, NOESY, HSQC, HMBC and Mass spectra also have been recorded. Elemental analysis was carried out for two compounds. Long range coupling is observed between -OH protons and H6a in all cases suggesting that -OH group is anti to C(5)-C(6) bond. In vitro biological applications like anti- inflammatory, antioxidant and antidiabetic activities were performed. It exhibited potent anti-inflammatory, good antioxidant and antidiabetic activities than standards. The interaction between enzyme ligands were identified with α-amylase (1HNY.pdb) using the AutoDock tools. Finally the HOMO, LUMO and molecular electrostatic potential (MEP) were performed by using DFT methods as additional support (Gaussian 09 W software)