Microwave-assisted synthesis and diabetic/antioxidant assessments of 1,3,2-benzothiazaphosphole-3(2H)-carbothioamide- and -diazaphosphole-3(2H)-dicarbothioamide 2-oxide derivatives

摘要

Environmentally friendly synthesis of 1,3,2-benzothiazaphosphole-3(2H)-carbothioamide and -diazaphosphole-3(2H)-dicarbothioamide 2-oxides or the carboxamide 2-oxide analogs was reported. The targets were accomplished via a two step process: (1) preparation of the substrates 2-phenyl-2,3-dihydro-1H-1,3,2-benzothiazaphosphole 2-oxide and -1,3,2-benzodiazaphosphole 2-oxide; (2) exploiting these two phospholes in reactions with various saturated and unsaturated isothiocyanates and some isocyanate analogs in dry DMF/pyridine under microwave irradiation thereby isolating the target compounds in 85-95 % yields. Based upon computer-assisted molecular model (CAMM), new compounds were screened for their antidiabetic and antioxidant properties and many of them exhibited moderate to high in vivo and in vitro diabetic and/or antioxidant potencies.