3-(1-(3-dimethylaminopropyl)-2-methyl-1H-indol-3-yl)propanoic acid | 1128165-48-9

• 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: 3-(1-(3-dimethylaminopropyl)-2-methyl-1H-indol-3-yl)propanoic acid
• 英文别名: 3-[1-[3-(Dimethylamino)propyl]-2-methylindol-3-yl]propanoic acid
• CAS: 1128165-48-9
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: UJHZEQSQEFRUHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1H-吲哚-3-丙酸 、 N,N-二甲基-3-氯丙胺 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以60%的产率得到3-(1-(3-dimethylaminopropyl)-2-methyl-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Inhibition of Dynamin Mediated Endocytosis by the Dynoles—Synthesis and Functional Activity of a Family of Indoles

  摘要：

  Screening identified two bisindolylmaleimides as 100 mu M inhibitors of the GTPase activity of dynamin I. Focused library approaches allowed development of indole-based dynamin inhibitors called dynoles. 100-Fold in vitro enhancement of potency was noted with the best inhibitor, 2-cyano-3-(1-(2-(dimethylamino)ethyl)- 1H-indol-3-yl)-N-octylacrylamide (dynole 34-2), a 1.3 +/- 0.3 mu M dynamin I inhibitor. Dynole 34-2 potently inhibited receptor mediated endocytosis (RME) internalization of Texas red-transferrin. The rank order of potency for a variety of dynole analogues on RME in U2OS cells matched their rank order for dynamin inhibition, suggesting that the mechanism of inhibition is via dynamin. Dynoles are the most active dynamin I inhibitors reported for in vitro or RME evaluations. Dynole 34-2 is 15-fold more active than dynasore against dynamin I and 6-fold more active against dynamin mediated RME (IC50 similar to 15 mu M; RME IC50 similar to 80 mu M). The dynoles represent a new series of tools to better probe endocytosis and dynamin-mediated trafficking events in a variety of cells.

  DOI：

  10.1021/jm900036m

文献信息

• [EN] INDOLE RELATED COMPOUNDS WITH PHYSIOLOGICAL ACTIVITY<br/>[FR] COMPOSÉS APPARENTÉS À L'INDOLE PRÉSENTANT UNE ACTIVITÉ PHYSIOLOGIQUE
  申请人：NEWCASTLE INNOVATION LTD

  公开号：WO2009034464A2

  公开（公告）日：2009-03-19

  The invention relates to compounds of Formula I or Ia having dynamin protein inhibitory activity. Compounds embodied by the invention have application in inhibiting cellular endocytosis and cytokinesis, and may be used in the prophylaxis or treatment of various diseases and conditions involving endocytosis or cell proliferation, such as seizures, epilepsy and cancer. Particularly preferred compounds provided by Formula I and Ia are indoles.