[1-(2-dimethylaminoethyl)-1H-indol-3-yl]acetic acid | 163838-65-1

• 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: [1-(2-dimethylaminoethyl)-1H-indol-3-yl]acetic acid
• 英文别名: [1-(2-dimethylaminoethyl)-3-indolyl]acetic acid；2-[1-[2-(Dimethylazaniumyl)ethyl]indol-3-yl]acetate
• CAS: 163838-65-1
• 化学式: C₁₄H₁₈N₂O₂
• mdl: MFCD06254340
• 分子量: 246.309
• InChiKey: DDACNPCNMZXVDM-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C(Solv: ethanol (64-17-5))
• 沸点：
  426.4±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-(2-dimethylaminoethyl)-1H-indol-3-yl]acetic acid 、 (3aR,4R,SR,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol 生成 (3aR,4R,SR,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(1-(2-dimethylaminoethyl)-3-indolyl)acetyl]perhydro-4,5-isoindolediol
  参考文献：
  名称：

  Perhydroisoindole derivatives, preparation thereof and pharmaceutical

  摘要：

  本发明涉及08/448,402号公式的全氢异吲哚衍生物（I），其中基团R为可选择性地2位或3位被卤素原子或甲基基团取代的苯基基团；R1为可选择性地被取代的苯基、环己二烯基、萘基、茚基或可选择性地被取代的杂环基；R2为氢、卤素、羟基、烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷氧基、烷硫基、酰氧基、羧基、可选择性地被取代的烷氧羰基、苄氧羰基、氨基或酰胺基；R3为可选择性地2位被取代的苯基；以及在适用情况下的盐类；及其制备方法。这些衍生物特别有用作为神经激肽A拮抗剂。 ##STR1##

  公开号：

  US05631279A1
• 作为产物：
  描述：

  3-吲哚乙酸 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以82%的产率得到[1-(2-dimethylaminoethyl)-1H-indol-3-yl]acetic 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

• US5631279A
  申请人：——

  公开号：US5631279A

  公开（公告）日：1997-05-20
• Inhibition of Dynamin Mediated Endocytosis by the <i>Dynoles</i>—Synthesis and Functional Activity of a Family of Indoles
  作者：Timothy A. Hill、Christopher P. Gordon、Andrew B. McGeachie、Barbara Venn-Brown、Luke R. Odell、Ngoc Chau、Annie Quan、Anna Mariana、Jennette A. Sakoff、Megan Chircop (nee Fabbro)、Phillip J. Robinson、Adam McCluskey

  DOI：10.1021/jm900036m

  日期：2009.6.25

  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.
• Perhydroisoindole derivatives, preparation thereof and pharmaceutical
  申请人：Rhone-Poulenc Rorer, S.A.

  公开号：US05631279A1

  公开（公告）日：1997-05-20

  This invention relates to perhydroisoindole derivatives of 08/448,402 formula (I), wherein radicals R are phenyl radicals optionally 2-or 3-substituted by a halogen atom or a methyl radical; R.sub.1 is optionally substituted phenyl, cyclohexadienyl, naphthyl, indenyl or optionally substituted heterocyclyl; R.sub.2 is H, halogen, OH, alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, acyloxy, acyloxy, carboxy, optionally substituted alkyloxycarbonyl, benzyloxycarbonyl, amino or acylamino; and R.sub.3 is optionally 2-substituted phenyl; optionally salts thereof where applicable; and preparation thereof. Said derivatives are particularly useful as neurokinin A antagonists. ##STR1##

  本发明涉及08/448,402号公式的全氢异吲哚衍生物（I），其中基团R为可选择性地2位或3位被卤素原子或甲基基团取代的苯基基团；R1为可选择性地被取代的苯基、环己二烯基、萘基、茚基或可选择性地被取代的杂环基；R2为氢、卤素、羟基、烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷氧基、烷硫基、酰氧基、羧基、可选择性地被取代的烷氧羰基、苄氧羰基、氨基或酰胺基；R3为可选择性地2位被取代的苯基；以及在适用情况下的盐类；及其制备方法。这些衍生物特别有用作为神经激肽A拮抗剂。 ##STR1##