A New Approach to Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3- methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Derivative

Two series, totalizing twelve, of new compounds, ethyl 1-aroyl/aroylmethyl-5-methyl-3- methylthiopyrazole-4-carboxylates 5/6, have been synthesized via highly regioselective acylation and alkylation of ethyl 3-methyl-5-methylthio-1H- pyrazole-4-carboxylate 2a with aroyl chloride 3 and alpha-tosyloxysubstitutedacetophenones 4. Unexpected structures of the product have been unambiguously determined by both X-ray crystallographic analysis and 2D NMR.

Design,synthesis and in vivo anti-hyperglycemic activity of gem-dimethyl-bearing C-glucosides as SGLT2 inhibitors

A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors,with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the key step.The in vivo anti-hyperglycemic activity was evaluated with mice oral glucose tolerance test（OGTT）,and all the synthesized compounds showed significant but less potent anti-hyperglycemic activity than the positive control dapagliflozin.