(E)-6-fluoro-3-(2-pyridin-4-ylvinyl)-1H-indole | 163239-23-4

• 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: (E)-6-fluoro-3-(2-pyridin-4-ylvinyl)-1H-indole
• 英文别名: 6-Fluoro-3-((E)-2-pyridin-4-yl-vinyl)-1H-indole；6-fluoro-3-[(E)-2-pyridin-4-ylethenyl]-1H-indole
• CAS: 163239-23-4
• 化学式: C₁₅H₁₁FN₂
• 分子量: 238.264
• InChiKey: UJTBWNKRXRHIGU-OWOJBTEDSA-N

物化性质

• 沸点：
  438.9±35.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-2-(4-fluoro-2-nitrophenyl)ethenylamine 在 哌啶 、 sodium hydroxide 、 镍 、 肼 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 (E)-6-fluoro-3-(2-pyridin-4-ylvinyl)-1H-indole
  参考文献：
  名称：

  Novel tryptophan dioxygenase inhibitors and combined tryptophan dioxygenase/5-HT reuptake inhibitors

  摘要：

  Tryptophan dioxygenase (TDO) is a liver enzyme that is responsible for the majority of the metabolism of tryptophan. A series of novel 3-(2-pyridylethenyl)indoles are shown to be potent inhibitors of TDO with selected members of the series also having 5-hydroxy tryptamine (5-HT) reuptake inhibitory activity. These compounds are shown to provide significant increases in the levels of tryptophan and 5-HT in the cerebrospinal fluid and are thus of interest for antidepressant therapy. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00124-2

文献信息

• Tryptophan 2,3-Dioxygenase (TDO) Inhibitors. 3-(2-(Pyridyl)ethenyl)indoles as Potential Anticancer Immunomodulators
  作者：Eduard Dolušić、Pierre Larrieu、Laurence Moineaux、Vincent Stroobant、Luc Pilotte、Didier Colau、Lionel Pochet、Benoît Van den Eynde、Bernard Masereel、Johan Wouters、Raphaël Frédérick

  DOI：10.1021/jm2006782

  日期：2011.8.11

  Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase (TDO), an unrelated hepatic enzyme also catalyzing the first step of tryptophan degradation, is also expressed in many tumors and that this expression prevents tumor rejection by locally depleting tryptophan. Herein, we report a structure- activity study on a series of 3-(2-(pyridyl)ethenyl)indoles. More than 70 novel derivatives were synthesized, and their TDO inhibitory potency was evaluated. The rationalization of the structure-activity relationships (SARs) revealed essential features to attain high TDO inhibition and notably a dense H-bond network mainly involving His(55) and Thr(254) residues. Our study led to the identification of a very promising compound (58) displaying good TDO inhibition (K-i = 5.5 mu M), high selectivity, and good oral bioavailability. Indeed, 58 was chosen for preclinical evaluation.
• METHODS AND COMPOSITIONS TO STABILIZE DIFFERENT STEM CELL STATES
  申请人：UNIVERSITY OF WASHINGTON - CENTER COMMERCIALIZATION

  公开号：US20170121678A1

  公开（公告）日：2017-05-04

  Provided herein are methods and compositions for maintaining human stem cells in either a nave state or a primed state, inducing, promoting, inhibiting, or controlling the transition from one state to another, and detecting the state of a stem cell. Also disclosed are compositions comprising substantially homogenous populations of primed state or nave state stem cells.
• [EN] TRYPTOPHAN CATABOLISM IN CANCER TREATMENT AND DIAGNOSIS<br/>[FR] CATABOLISME DU TRYPTOPHANE DANS LE TRAITEMENT ET LE DIAGNOSTIC DU CANCER
  申请人：LUDWIG INST FOR CANCER RES LTD

  公开号：WO2010008427A1

  公开（公告）日：2010-01-21

  The unexpected expression of tryptophan 2,3-dioxygenase (TD02)in cancer cells and tumors has been established. Methods for diagnosing cancer based on the expression of TD02 are provided, as are methods for treating cancer and inhibiting the growth of cancer cells by inhibiting TD02, as well as pharmaceutical compositions.
• Novel tryptophan dioxygenase inhibitors and combined tryptophan dioxygenase/5-HT reuptake inhibitors
  作者：D.J. Madge、R. Hazelwood、R. Iyer、H.T. Jones、M. Salter

  DOI：10.1016/0960-894x(96)00124-2

  日期：1996.4

  Tryptophan dioxygenase (TDO) is a liver enzyme that is responsible for the majority of the metabolism of tryptophan. A series of novel 3-(2-pyridylethenyl)indoles are shown to be potent inhibitors of TDO with selected members of the series also having 5-hydroxy tryptamine (5-HT) reuptake inhibitory activity. These compounds are shown to provide significant increases in the levels of tryptophan and 5-HT in the cerebrospinal fluid and are thus of interest for antidepressant therapy. Copyright (C) 1996 Elsevier Science Ltd