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

Molecular Biology

Journal of Cell Science & Therapy

Author(s): He YW, Cao LH, Zhang JB, Wang DZ, Aisa HA, He YW, Cao LH, Zhang JB, Wang DZ, Aisa HA, He YW, Cao LH, Zhang JB, Wang DZ, Aisa HA, He YW, Cao LH, Zhang JB, Wang DZ, Aisa HA

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Abstract 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 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. Copyright © 2011 Elsevier Ltd. All rights reserved. This article was published in Carbohydr Res and referenced in Journal of Cell Science & Therapy

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