5-chloro-1,4-dihydro-6-(indol-7-yl)-2,2,4,4,8-pentamethyl-2H-quinolin-3-one | 877160-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-chloro-1,4-dihydro-6-(indol-7-yl)-2,2,4,4,8-pentamethyl-2H-quinolin-3-one
• 英文别名: 5-chloro-6-(1H-indol-7-yl)-2,2,4,4,8-pentamethyl-1,2-dihydroquinolin-3(4H)-one；5-chloro-6-(1H-indol-7-yl)-2,2,4,4,8-pentamethyl-1H-quinolin-3-one
• CAS: 877160-79-7
• 化学式: C₂₂H₂₃ClN₂O
• 分子量: 366.89
• InChiKey: FAZOJHMTURPXLD-UHFFFAOYSA-N

物化性质

• 沸点：
  532.2±50.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-1,4-dihydro-6-(indol-7-yl)-2,2,4,4,8-pentamethyl-2H-quinolin-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (+/-)-5-chloro-1,2,3,4-tetrahydro-3-hydroxy-6-(indol-7-yl)-2,2,4,4,8-pentamethylquinoline
  参考文献：
  名称：

  Tetrahydroquinoline glucocorticoid receptor agonists: Discovery of a 3-hydroxyl for improving receptor selectivity

  摘要：

  We have previously disclosed a series of glucocorticoid receptor (GR) ligands derived from 6-indole-1,2,3,4-tetrahydroquinolines through structure-activity relationship (SAR) of the pendent C6-indole ring. In parallel with this effort, we now report SAR of the tetrahydroquinoline A-ring that identified the importance of a C3 hydroxyl in improving GR selectivity within a series of non-steroidal GR agonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.047
• 作为产物：
  描述：

  6-bromo-5-chloro-1,4-dihydro-2,2,4,4,8-pentamethyl-2H-quinolin-3-one 、 吲哚-7-硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-chloro-1,4-dihydro-6-(indol-7-yl)-2,2,4,4,8-pentamethyl-2H-quinolin-3-one
  参考文献：
  名称：

  Tetrahydroquinoline glucocorticoid receptor agonists: Discovery of a 3-hydroxyl for improving receptor selectivity

  摘要：

  We have previously disclosed a series of glucocorticoid receptor (GR) ligands derived from 6-indole-1,2,3,4-tetrahydroquinolines through structure-activity relationship (SAR) of the pendent C6-indole ring. In parallel with this effort, we now report SAR of the tetrahydroquinoline A-ring that identified the importance of a C3 hydroxyl in improving GR selectivity within a series of non-steroidal GR agonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.047

文献信息

• [EN] INTRACELLULAR RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS MODULATEURS DE RÉCEPTEURS INTRACELLULAIRES ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION DE CEUX-CI
  申请人：LIGAND PHARM INC

  公开号：WO2006019716A1

  公开（公告）日：2006-02-23

  This invention relates to compounds of Formula I, II or III with the definitions of R1-R10 according to claim 1 that bind to intracellular receptors and/or modulate activity of intracellular receptors, and to methods for making and using such compounds.

  这项发明涉及具有根据权利要求1中R1-R10的定义的化合物I、II或III，这些化合物与细胞内受体结合和/或调节细胞内受体活性，并涉及制备和使用这类化合物的方法。
• INTRACELLULAR RECEPTOR MODULATOR COMPOUNDS AND METHODS
  申请人：Higuchi I. Robert

  公开号：US20070254917A1

  公开（公告）日：2007-11-01

  This invention relates to compounds that bind to intracellular receptors and/or modulate activity of intracellular receptors, and to methods for making and using such compounds.

  本发明涉及与细胞内受体结合和/或调节细胞内受体活性的化合物，以及制备和使用这种化合物的方法。
• Tetrahydroquinoline glucocorticoid receptor agonists: Discovery of a 3-hydroxyl for improving receptor selectivity
  作者：Steven L. Roach、Robert I. Higuchi、Andrew R. Hudson、Mark E. Adams、Peter M. Syka、Dale E. Mais、Jeffrey N. Miner、Keith B. Marschke、Lin Zhi

  DOI：10.1016/j.bmcl.2010.11.047

  日期：2011.1

  We have previously disclosed a series of glucocorticoid receptor (GR) ligands derived from 6-indole-1,2,3,4-tetrahydroquinolines through structure-activity relationship (SAR) of the pendent C6-indole ring. In parallel with this effort, we now report SAR of the tetrahydroquinoline A-ring that identified the importance of a C3 hydroxyl in improving GR selectivity within a series of non-steroidal GR agonists. (C) 2010 Elsevier Ltd. All rights reserved.