5-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)-N-β-D-xylopyranosyl-1,3,4-thiadiazol-2-amine | 1231978-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)-N-β-D-xylopyranosyl-1,3,4-thiadiazol-2-amine
• 英文别名: (2R,3R,4S,5R)-2-[[5-[(1-phenyltetrazol-5-yl)sulfanylmethyl]-1,3,4-thiadiazol-2-yl]amino]oxane-3,4,5-triol
• CAS: 1231978-22-5
• 化学式: C₁₅H₁₇N₇O₄S₂
• 分子量: 423.476
• InChiKey: QYVUWOXCHNKGQF-GWNIPJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  205
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (1-phenyl-1H-tetrazol-5-ylthiol)acetic acid hydrazide 在 甲醇 、 磷酸 、 sodium methylate 、 乙酸酐 作用下， 以 苯 为溶剂， 反应 28.5h， 生成 5-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)-N-β-D-xylopyranosyl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  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-beta-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-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 CH3ONa/CH3OH. All of the novel compounds were characterized by IR. H-1 NMR, C-13 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. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.010