3-(β-D-glucopyranosyl)-5-phenylisoxazole | 1819334-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(β-D-glucopyranosyl)-5-phenylisoxazole
• 英文别名: D-Glucitol, 1,5-anhydro-1-C-(5-phenyl-3-isoxazolyl)-, (1S)-；(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-(5-phenyl-1,2-oxazol-3-yl)oxane-3,4,5-triol
• CAS: 1819334-25-2
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: NHURPYHRQRHSIG-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-phenyl-3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)isoxazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以82%的产率得到3-(β-D-glucopyranosyl)-5-phenylisoxazole
  参考文献：
  名称：

  4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase

  摘要：

  Inhibition of glycogen phosphorylases may lead to pharmacological treatments of diseases in which glycogen metabolism plays an important role: first of all in diabetes, but also in cardiovascular and tumorous disorders. C-(beta-D-Glucopyranosyl) isoxazole, pyrazole, thiazole, and imidazole type compounds were synthesized, and the latter showed the strongest inhibition against rabbit muscle glycogen phosphorylase b. Most efficient was 2-(beta-D-glucopyranosyl)-4(5)-(2-naphthyl)-imidazole (11b, K-i = 31 nM) representing the best nanomolar glucose derived inhibitor of the enzyme.

  DOI：

  10.1021/acsmedchemlett.5b00361