1-(β-D-glucopyranosyl)benzimidazolin-2-one

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(β-D-glucopyranosyl)benzimidazolin-2-one
• 英文别名: 3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-benzimidazol-2-one
• 化学式: C₁₃H₁₆N₂O₆
• 分子量: 296.28
• InChiKey: CWOLCJVCLXGDPO-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羟基苯并咪唑 在 吡啶 、 potassium cyanide 、 mercury(II) diacetate 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.0h， 生成 1-(β-D-glucopyranosyl)benzimidazolin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives

  摘要：

  The synthesis of new oxindoles and benzimidazolinones derivatives bearing a sugar residue on the aromatic nitrogen is described. The presence of the glycoside moiety should enhance the solubility of these heterocyclic compounds and/or improve the interaction with the active site of the biological targets. The inhibitory activities of these new compounds toward five kinases were examined: KDR (VEGFR-2), FGFR-1, PDGFR-beta, EGFR and Tie 2. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.01.001

文献信息

• Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives
  作者：Samir Messaoudi、Martine Sancelme、Valérie Polard-Housset、Bettina Aboab、Pascale Moreau、Michelle Prudhomme

  DOI：10.1016/j.ejmech.2004.01.001

  日期：2004.5

  The synthesis of new oxindoles and benzimidazolinones derivatives bearing a sugar residue on the aromatic nitrogen is described. The presence of the glycoside moiety should enhance the solubility of these heterocyclic compounds and/or improve the interaction with the active site of the biological targets. The inhibitory activities of these new compounds toward five kinases were examined: KDR (VEGFR-2), FGFR-1, PDGFR-beta, EGFR and Tie 2. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans. (C) 2004 Elsevier SAS. All rights reserved.