Synthesis of variously coupled conjugates of d-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase

Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase

“…33 Reactions of 7 with non-purified N-benzyl-arenecarboximidoyl For the preparation of xylopyranosylidene-spiro-isoxazolines P, O-peracetylated b-D-xylopyranosyl cyanide 34 20 was transformed to the corresponding anhydro-aldose tosylhydrazone 21 by applying our published method. 35,36 Bamford-Stevens reaction 37 Synthesis of the xylopyranosylidene-spiro-oxathiazoles Q was started by the conversion of O-peracetylated 1-thio-b-D-xylopyranose 41 35 to S-b-D-xylopyranosyl thiohydroximates 36-38 (Scheme 4).…”

New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase

“…Syntheses of the target compounds were started by the preparation of O-protected Cglucopyranosyl-tetrazole 1 (Table 1) from 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide [61] according to our recent procedure [27]. N-Benzyl arenecarboxamides 2, obtained from the corresponding acid chloride and benzylamine, were converted to imidoyl chlorides by SOCl 2 which were then reacted without purification with tetrazole 1 in a one-pot fashion to M A N U S C R I P T 6 give 4-benzyl-1,2,4-triazole derivatives 3.…”

Latest Update on Pharmacological Activities of 1,3,4-Oxadiazole Derivatives

“…Some synthesis a series of 2-(β-D-Glucopyranosyl)-5-(4,-hydroxymethyl-1,2,3-triazol-1,-ylmethyl)-1,3,4-oxadiazole derivativeshas been also found to possess antidiabetes [33] (Figure 33). …”