Synthesis and bioactivity of 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N- xylopyranosyl-1,3,4-oxa(thia)diazol-2-amines

摘要

A series of new N′-[N-(2,3,4-tri-O-acetyl-β-d-xylopyranosyl) thiocarbamoyl]-2-[(1-aryl-1H-tetrazol-5-yl)sulfanyl]acetohydrazides 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-β-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-β-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-β-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 CH3ONa/CH3OH. All of the novel compounds were characterized by IR, 1H NMR, 13C 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.