Synthesis and bioactivity of 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-xylopyranosyl-1,3,4-oxa(thia)diazol-2-amines |
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| Authors: | He Yao-Wu Cao Ling-Hua Zhang Jian-Bin Wang Duo-Zhi Aisa Haji Akber |
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| Institution: | aKey Laboratory of Chemistry of Plant Resources in Arid Regions, Chinese Academy of Sciences, Xinjiang Technical Institute of Physics and Chemistry, Urumqi 830011, PR China;bCollege of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, PR China;cPhysics and Chemistry Test Center of Xinjiang University, Urumqi 830046, PR China;dGraduate University of the Chinese Academy of Sciences, Beijing 100049, PR China |
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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 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. |
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| Keywords: | Aryltetrazole Xylopyranosyl isothiocyanate Oxadiazole Thiadiazole Crystal structure Biological activity |
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