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Synthesis of novel glycosyl-1,2,3-1H-triazolyl methyl quinazolin-4(3H)-ones and their effect on GLUT4 translocation

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Cu(OTf)2 catalyzed synthesis of propargylated 2,3-dihydroquinazolin-4(1H)-ones has been accomplished from 2-amino-N-propargyl benzamides and aromatic aldehydes under MW irradiation. Next, a series of novel glycosyl triazolyl methyl quinazolin-4(3H)-ones have been synthesized… Click to show full abstract

Cu(OTf)2 catalyzed synthesis of propargylated 2,3-dihydroquinazolin-4(1H)-ones has been accomplished from 2-amino-N-propargyl benzamides and aromatic aldehydes under MW irradiation. Next, a series of novel glycosyl triazolyl methyl quinazolin-4(3H)-ones have been synthesized by CuAAC reaction of propargylated 2,3-dihydroquinazolin-4(1H)-ones with glycosyl azides followed by iodine mediated oxidation. In this series, six compounds showed promising to significant GLUT4 translocation activity comparable to rosiglitazone.

Keywords: novel glycosyl; glut4 translocation; triazolyl methyl; quinazolin ones; methyl quinazolin; glycosyl triazolyl

Journal Title: Tetrahedron
Year Published: 2017

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