Synthesis and Antiglycating Activity of 2-Aminopropylmorpholino-5-Aryl-6H-1,3,4-Thiadiazine Dihydrobromides and 2-Aminopropylmopholino-5-Thienyl-6H-1,3,4-Thiadiazine Dihydrobromides

A group of novel 2-propylmorpholino-5-aryl- and 5-thienyl-6H-1,3,4-thiadiazine dihydrobromides was synthesized by cyclocondensation of 4-[3-(4-morpholino)propyl]-3-thiosemicarbazide with α –haloacetoarenones or α-haloacetylthiophenones. Two compounds of this group were found to produce effective inhibition of non-enzymatic protein glycation in an in vitro model system. These test results indicate that compounds IIIa and IIIc, which contain phenyl- and 4′ -chlorophenyl groups at position 5 of the thiadiazine ring respectively, are candidates for in vivo studies.