N-(2,3,3-trimethyl-3H-indol-5-yl)acetamide | 41382-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(2,3,3-trimethyl-3H-indol-5-yl)acetamide
• 英文别名: N-(2,3,3-trimethyl-1,2-dihydroindol-5-yl)acetamide
• CAS: 41382-30-3
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: WKKWUGUBWFCZCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,3,3-trimethyl-3H-indol-5-yl)acetamide 在 盐酸 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 5.5h， 生成 N,2,3,3-tetramethyl-3H-indol-5-amine
  参考文献：
  名称：

  Solvent-Sensitive Dyes to Report Protein Conformational Changes in Living Cells

  摘要：

  Covalent attachment of solvent-sensitive fluorescent dyes to proteins is a powerful tool for studying protein conformational changes, ligand binding, or posttranslational modifications. We report here new merocyanine dyes that make possible the quantitation of such protein activities in individual living cells. The quantum yield of the new dyes is sharply dependent on solvent polarity or viscosity, enabling them to report changes in their protein environment. This is combined with other stringent requirements needed in a live cell imaging dye, including appropriate photophysical properties (excitation >590 nm, high fluorescence quantum yield, high extinction coefficient), good photostability, minimal aggregation in water, and excellent water solubility. The dyes were derivatized with iodoacetamide and succinimidyl ester side chains for site-selective covalent attachment to proteins. A novel biosensor of Cdc42 activation made with one of the new dyes showed a 3-fold increase in fluorescence intensity in response to GTP-binding by Cdc42. The dyes reported here should be useful in the preparation of live cell biosensors for a diverse range of protein activities.

  DOI：

  10.1021/ja0290882
• 作为产物：
  描述：

  乙酸酐 、 2,3,3-trimethyl-3H-indol-5-amine 反应 0.33h， 以60%的产率得到N-(2,3,3-trimethyl-3H-indol-5-yl)acetamide
  参考文献：
  名称：

  Solvent-Sensitive Dyes to Report Protein Conformational Changes in Living Cells

  摘要：

  Covalent attachment of solvent-sensitive fluorescent dyes to proteins is a powerful tool for studying protein conformational changes, ligand binding, or posttranslational modifications. We report here new merocyanine dyes that make possible the quantitation of such protein activities in individual living cells. The quantum yield of the new dyes is sharply dependent on solvent polarity or viscosity, enabling them to report changes in their protein environment. This is combined with other stringent requirements needed in a live cell imaging dye, including appropriate photophysical properties (excitation >590 nm, high fluorescence quantum yield, high extinction coefficient), good photostability, minimal aggregation in water, and excellent water solubility. The dyes were derivatized with iodoacetamide and succinimidyl ester side chains for site-selective covalent attachment to proteins. A novel biosensor of Cdc42 activation made with one of the new dyes showed a 3-fold increase in fluorescence intensity in response to GTP-binding by Cdc42. The dyes reported here should be useful in the preparation of live cell biosensors for a diverse range of protein activities.

  DOI：

  10.1021/ja0290882

文献信息

• US4145537A
  申请人：——

  公开号：US4145537A

  公开（公告）日：1979-03-20