2-[2-(1H-benzimidazol-2-ylsulfanyl)ethoxy]benzaldehyde | 247114-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[2-(1H-benzimidazol-2-ylsulfanyl)ethoxy]benzaldehyde
• CAS: 247114-45-0
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: GQRVJJVLCZAZCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(1H-benzimidazol-2-ylsulfanyl)ethoxy]benzaldehyde 、 氰乙酰胺 在 β-丙氨酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以25%的产率得到(E)-3-{2-[2-(1H-Benzoimidazol-2-ylsulfanyl)-ethoxy]-phenyl}-2-cyano-acrylamide
  参考文献：
  名称：

  α-Cyanocinnamide derivatives: a new family of non-peptide, non-sulfhydryl inhibitors of ras farnesylation

  摘要：

  Farnesylation of Ras and other proteins is required for their membrane attachment and normal function. Here we report on the synthesis of alpha-cyanocinnamide derivatives, a new family of farnesyltransferase inhibitors. These compounds are nonpeptidic and do not contain sulfhydryl groups. The most potent compound is a pure competitive inhibitor with respect to the Ras protein and mixed competitive with respect to farnesyl diphosphate. Selectivity studies against geranylgeranyltransferase and biological activities of selected compounds are described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00118-2
• 作为产物：
  描述：

  邻甲基苄醇 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 34.0h， 生成 2-[2-(1H-benzimidazol-2-ylsulfanyl)ethoxy]benzaldehyde
  参考文献：
  名称：

  α-Cyanocinnamide derivatives: a new family of non-peptide, non-sulfhydryl inhibitors of ras farnesylation

  摘要：

  Farnesylation of Ras and other proteins is required for their membrane attachment and normal function. Here we report on the synthesis of alpha-cyanocinnamide derivatives, a new family of farnesyltransferase inhibitors. These compounds are nonpeptidic and do not contain sulfhydryl groups. The most potent compound is a pure competitive inhibitor with respect to the Ras protein and mixed competitive with respect to farnesyl diphosphate. Selectivity studies against geranylgeranyltransferase and biological activities of selected compounds are described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00118-2

文献信息

• α-Cyanocinnamide derivatives: a new family of non-peptide, non-sulfhydryl inhibitors of ras farnesylation
  作者：Enrique Poradosu、Aviv Gazit、Hadas Reuveni、Alexander Levitzki

  DOI：10.1016/s0968-0896(99)00118-2

  日期：1999.8

  Farnesylation of Ras and other proteins is required for their membrane attachment and normal function. Here we report on the synthesis of alpha-cyanocinnamide derivatives, a new family of farnesyltransferase inhibitors. These compounds are nonpeptidic and do not contain sulfhydryl groups. The most potent compound is a pure competitive inhibitor with respect to the Ras protein and mixed competitive with respect to farnesyl diphosphate. Selectivity studies against geranylgeranyltransferase and biological activities of selected compounds are described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.