(4-{[4-(2-hydroxyethyl)piperazin-1-yl]carbonyl}phenyl)boronic acid | 913943-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-{[4-(2-hydroxyethyl)piperazin-1-yl]carbonyl}phenyl)boronic acid
• 英文别名: 4-(4-(2-hydroxyethyl)piperazine-1-carbonyl)phenylboronic acid；[4-[4-(2-hydroxyethyl)piperazine-1-carbonyl]phenyl]boronic acid
• CAS: 913943-06-3
• 化学式: C₁₃H₁₉BN₂O₄
• 分子量: 278.116
• InChiKey: PKQLDPHGOUXRBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.88
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-bromo-1-methyl-1-H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 、 (4-{[4-(2-hydroxyethyl)piperazin-1-yl]carbonyl}phenyl)boronic acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 生成 4-(4-(4-(2-hydroxyethyl)piperazine-1-carbonyl)phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
  参考文献：
  名称：

  Discovery and optimization of 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

  摘要：

  Wediscovered 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR). Since phenolic OH groups pose metabolic liability, one of the two hydroxyl groups was selectively removed. The SAR data showed the structural features necessary for subnanomolar inhibitory activity against mTOR kinase as well as selectivity over PI3K alpha. An X-ray co-crystal structure of one inhibitor with the mTOR-related PI3K gamma revealed the key hydrogen bonding interactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.135

文献信息

• SUBSTITUTED PHENYLALANINE DERIVATIVES
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160244437A1

  公开（公告）日：2016-08-25

  The invention relates to substituted phenylalanine derivatives and to processes for preparation thereof, and to the use thereof for production of medicaments for the treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and/or severe perioperative blood loss.

  本发明涉及取代苯丙氨酸衍生物及其制备方法，以及将其用于生产用于治疗和/或预防疾病的药物，特别是心血管疾病和/或严重围手术期失血的药物。
• AURORA KINASE INHIBITORS
  申请人：Zhuang Linghang

  公开号：US20110136766A1

  公开（公告）日：2011-06-09

  Disclosed herein are Aurora kinase Inhibitors represented by Structural Formula (I): Values for the variables in Structural Formula (I) are defined herein.

  本文披露的是由结构式（I）表示的极光激酶抑制剂：结构式（I）中的变量值在此定义。
• [EN] AURORA KINASE INHIBITORS<br/>[FR] INHIBITEUR DE L'AURORA KINASE
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2009111028A8

  公开（公告）日：2009-11-26
• Discovery and optimization of 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)
  作者：Hwei-Ru Tsou、Gloria MacEwan、Gary Birnberg、George Grosu、Matthew G. Bursavich、Joel Bard、Natasja Brooijmans、Lourdes Toral-Barza、Irwin Hollander、Tarek S. Mansour、Semiramis Ayral-Kaloustian、Ker Yu

  DOI：10.1016/j.bmcl.2010.01.135

  日期：2010.4

  Wediscovered 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR). Since phenolic OH groups pose metabolic liability, one of the two hydroxyl groups was selectively removed. The SAR data showed the structural features necessary for subnanomolar inhibitory activity against mTOR kinase as well as selectivity over PI3K alpha. An X-ray co-crystal structure of one inhibitor with the mTOR-related PI3K gamma revealed the key hydrogen bonding interactions. (C) 2010 Elsevier Ltd. All rights reserved.