A series of new N'-N-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)thiocarbamoyl-2-(1-aryl-1H-tetrazol-5-yl) sulfanylacetohydrazides 5a-5e were synthesized rapidly in high yields from 2-(1-aryl-1H-tetrazol-5-ylsulfanyl)acetohydrazides 3a-3e and 2,3,4-tri-O-acetyl-beta-D-xylopyranosyl isothiocyanate 4, then 5a-5e were converted to a series of new 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)-1,3,4-oxadiazole-2-amines 6a-6e and 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)-1,3,4-thiadiazole-2-amines 7a-7e, respectively under mercuric acetate/alcohol system or acetic anhydride/phosphoric acid system, then deacetylated in the solution of CH(3)ONa/CH(3)OH. All of the novel compounds were characterized by IR. (1)H NMR, (13)C NMR, MS and elemental analysis. The structures of compounds 2e, 3e, 5a and 5c have been determined by X-ray diffraction analysis. Some of the synthesized compounds displayed PTP1B inhibition and microorganism inhibition.
Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Chem Plant Resources Arid Reg, Urumqi 830011, Peoples R China;Xinjiang Univ, Coll Chem & Chem Engn, Urumqi 830046, Peoples R China;Xinjiang Univ, Phys & Chem Test Ctr, Urumqi 830046, Peoples R China;Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
He Yao-Wu,Cao Ling-Hua,Zhang Jian-Bin,et al. Synthesis and bioactivity of 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-xylopyranosyl-1,3,4-oxa(thia)diazol-2-amines[J]. CARBOHYDRATE RESEARCH,2011,346(5):551-559.