1-phenylacetyl-2,3-dihydro-1H-indole-2-carboxylic acid | 167633-66-1

• 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-phenylacetyl-2,3-dihydro-1H-indole-2-carboxylic acid
• 英文别名: 1-(2-Phenylacetyl)-2,3-dihydroindole-2-carboxylic acid
• CAS: 167633-66-1
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: VZLNFICIEVILIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenylacetyl-2,3-dihydro-1H-indole-2-carboxylic acid 、 甲胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 反应 0.5h， 生成 C₁₈H₁₈N₂O₂
  参考文献：
  名称：

  Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of Trypanosoma brucei

  摘要：

  There is an urgent need for new, brain penetrant small molecules that target the central nervous system second stage of human African trypanosomiasis (HAT). We report that a series of novel indoline-2carboxamides have been identified as inhibitors of Trypanosoma brucei from screening of a focused protease library against Trypanosoma brucei brucei in culture. We describe the optimization and characterization of this series. Potent antiproliferative activity was observed. The series demonstrated excellent pharmacokinetic properties, full cures in a stage 1 mouse model of HAT, and a partial cure in a stage 2 mouse model of HAT. Lack of tolerability prevented delivery of a fully curative regimen in the stage 2 mouse model and thus further progress of this series.

  DOI：

  10.1021/acs.jmedchem.5b00596
• 作为产物：
  描述：

  2,3-二氢-1H-吲哚-2-羧酸甲酯 、 苯乙酰氯 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 1-phenylacetyl-2,3-dihydro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Tetracyclic condensed heterocyclic compounds and their use

  摘要：

  该化合物的式子为##STR1## 其中Ar代表一个四环融合的杂环基团，可以被取代；R.sup.1代表氢或一个可以被取代的碳氢基团；Y代表一个氨基或含氮的饱和杂环基团，可以被取代，它的盐具有优异的胆碱酯酶抑制活性和单胺摄取抑制活性，因此可用作治疗和/或预防老年性痴呆的药物。

  公开号：

  US05620973A1

文献信息

• Tetracyclic condensed heterocyclic compounds for the treatment of senile dementia
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0655451A1

  公开（公告）日：1995-05-31

  A novel compound of the formula wherein Ar represents a tetracyclic fused heterocyclic group which may be substituted; R¹ represents H or a hydrocarbon group which may be substituted; Y represents an amino or nitrogen-containing saturated heterocyclic group which may be substituted, its salt, inhibiting excellent cholinesterase inhibitory activity and monoamine uptake inhibitory activity, thus being useful as therapeutic and/or prophylactic medicaments of senile dementia.

  一种新颖的式化合物 其中 Ar 代表可被取代的四环融合杂环基团；R¹ 代表 H 或可被取代的烃基团；Y 代表可被取代的氨基或含氮饱和杂环基团，其盐具有优异的胆碱酯酶抑制活性和单胺摄取抑制活性，因此可用作老年痴呆症的治疗和/或预防药物。
• US5620973A
  申请人：——

  公开号：US5620973A

  公开（公告）日：1997-04-15
• US5814642A
  申请人：——

  公开号：US5814642A

  公开（公告）日：1998-09-29
• Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of <i>Trypanosoma brucei</i>
  作者：Laura A. T. Cleghorn、Sébastien Albrecht、Laste Stojanovski、Frederick R. J. Simeons、Suzanne Norval、Robert Kime、Iain T. Collie、Manu De Rycker、Lorna Campbell、Irene Hallyburton、Julie A. Frearson、Paul G. Wyatt、Kevin D. Read、Ian H. Gilbert

  DOI：10.1021/acs.jmedchem.5b00596

  日期：2015.10.8

  There is an urgent need for new, brain penetrant small molecules that target the central nervous system second stage of human African trypanosomiasis (HAT). We report that a series of novel indoline-2carboxamides have been identified as inhibitors of Trypanosoma brucei from screening of a focused protease library against Trypanosoma brucei brucei in culture. We describe the optimization and characterization of this series. Potent antiproliferative activity was observed. The series demonstrated excellent pharmacokinetic properties, full cures in a stage 1 mouse model of HAT, and a partial cure in a stage 2 mouse model of HAT. Lack of tolerability prevented delivery of a fully curative regimen in the stage 2 mouse model and thus further progress of this series.
• Tetracyclic condensed heterocyclic compounds and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05620973A1

  公开（公告）日：1997-04-15

  A novel compound of the formula ##STR1## wherein Ar represents a tetracyclic fused heterocyclic group which may be substituted; R.sup.1 represents H or a hydrocarbon group which may be substituted; Y represents an amino or nitrogen-containing saturated heterocyclic group which may be substituted, its salt, inhibiting excellent cholinesterase inhibitory activity and monoamine uptake inhibitory activity, thus being useful as therapeutic and/or prophylactic medicaments of senile dementia.

  该化合物的式子为##STR1## 其中Ar代表一个四环融合的杂环基团，可以被取代；R.sup.1代表氢或一个可以被取代的碳氢基团；Y代表一个氨基或含氮的饱和杂环基团，可以被取代，它的盐具有优异的胆碱酯酶抑制活性和单胺摄取抑制活性，因此可用作治疗和/或预防老年性痴呆的药物。