Synthesis of novel β-aminoalcohols containing nabumetone moiety with potential antidiabetic activity

Twenty five new β-aminoalcohols containing nabumetone moiety were prepared via the reduction of potassium borohydride with a convenient and efficient procedure, starting from β-aminoketones that have been synthesized by our group.  Their chemical structures were determined by IR, MS, ¹H NMR, ¹³C NMR, HR-MS and antidiabetic activities were screened in vitro.  Preliminary results revealed that the antidiabetic activity of most β-aminoalcohols were better than that of the corresponding β-aminoketones.  Although most compounds showed weak antidiabetic activity, the α-glucosidase inhibitory activity of compounds 5hd¹ and 5id² reached 74.37% and 90.15%, respectively, which were superior to the positive control.  The relative peroxisome proliferator-activated receptor response element (PPRE) activity of five compounds were more than 60%, among them compound 5ca possessed the highest activity (112.59%).  As lead molecules of antidiabetic agents, compounds 5hd¹, 5id² and 5ca deserve further study.