title: Synthesis and bioactivity of 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-xylopyranosyl-1,3,4-oxa(thia)diazol-2-amines.
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.
authors.affiliation: Key Laboratory of Chemistry of Plant Resources in Arid Regions, Chinese Academy of Sciences, Xinjiang Technical Institute of Physics and Chemistry, Urumqi 830011, PR China.
authors.forename: Yao-Wu
authors.initials: YW
authors.lastname: He
authors.forename: Ling-Hua
authors.initials: LH
authors.lastname: Cao
authors.forename: Jian-Bin
authors.initials: JB
authors.lastname: Zhang
authors.forename: Duo-Zhi
authors.initials: DZ
authors.lastname: Wang
authors.forename: Haji Akber
authors.initials: HA
authors.lastname: Aisa
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D017879:Isothiocyanates; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010069:Oxadiazoles; D013211:Staphylococcus aureus / Q000187:drug effects; D013777:Tetrazoles / Q000737:chemistry*; D013830:Thiadiazoles / Q000737:chemistry; D014961:X-Ray Diffraction; D014994:Xylose / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D000588:Amines; D000890:Anti-Infective Agents; D017879:Isothiocyanates; D010069:Oxadiazoles; D013777:Tetrazoles; D013830:Thiadiazoles; C045574:1H-tetrazole; C037152:isothiocyanic acid; D014994:Xylose