5-(4-amino-2-(N-ethylcarboxamido-phenoxy))-3-chloropyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-amino-2-(N-ethylcarboxamido-phenoxy))-3-chloropyridine
• 英文别名: N-ethyl 5-amino-2-(3-chloro-5-pyridyloxy)benzamide；5-amino-2-(5-chloropyridin-3-yl)oxy-N-ethylbenzamide
• 化学式: C₁₄H₁₄ClN₃O₂
• 分子量: 291.737
• InChiKey: OIKNAPHXSXBACW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对叔丁基苯磺酰氯 、 5-(4-amino-2-(N-ethylcarboxamido-phenoxy))-3-chloropyridine 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 5-[(4-tert-butylphenyl)sulfonylamino]-2-(5-chloropyridin-3-yl)oxy-N-ethylbenzamide
  参考文献：
  名称：

  Discovery of INT131: A selective PPARγ modulator that enhances insulin sensitivity

  摘要：

  PPAR gamma is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPAR gamma modulators (SPPAR gamma Ms) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPAR gamma full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPAR gamma partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.058
• 作为产物：
  描述：

  5-氯-3-羟基吡啶 在 tin(II) chloride dihdyrate 、 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-amino-2-(N-ethylcarboxamido-phenoxy))-3-chloropyridine
  参考文献：
  名称：

  Discovery of INT131: A selective PPARγ modulator that enhances insulin sensitivity

  摘要：

  PPAR gamma is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPAR gamma modulators (SPPAR gamma Ms) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPAR gamma full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPAR gamma partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.058

文献信息

• Therapeutic modulation of PPARgamma activity
  申请人：Chen Jin-Long

  公开号：US20050250820A1

  公开（公告）日：2005-11-10

  Modulators of PPARγ activity are used in methods of treating and/or preventing conditions such as osteoporosis, Alzheimer's disease, psoriasis and acne, and cancer.

  PPARγ活性调节剂被用于治疗和/或预防骨质疏松症、阿尔茨海默病、银屑病和痤疮以及癌症等疾病的方法中。
• PPARgamma modulators
  申请人：Tularik Inc.

  公开号：US20030088103A1

  公开（公告）日：2003-05-08

  Modulators of PPAR&ggr; activity are provided which are useful in pharmaceutical compositions and methods for the treatment of conditions such as type II diabetes and obesity.

  提供了PPAR&ggr;活性的调节剂，可用于制备药物组合物和治疗2型糖尿病和肥胖症等病症的方法。
• PPAR-&ggr; modulators
  申请人：Tularik Inc.

  公开号：US06200995B1

  公开（公告）日：2001-03-13

  Modulators of PPAR&ggr; activity are provided which are useful in pharmaceutical compositions and methods for the treatment of conditions such as type II diabetes and obesity.

  提供了PPAR&ggr;活性调节剂，可用于制备药物组合物并治疗诸如2型糖尿病和肥胖症等疾病的方法。
• PPARγ modulators
  申请人：Amgen Inc.

  公开号：US07439242B2

  公开（公告）日：2008-10-21

  Modulators of PPARγ activity are provided which are useful in pharmaceutical compositions and methods for the treatment of conditions such as type II diabetes and obesity.

  提供了PPARγ活性的调节剂，这些调节剂在制药组合物和治疗II型糖尿病和肥胖症等疾病的方法中非常有用。
• Discovery of INT131: A selective PPARγ modulator that enhances insulin sensitivity
  作者：Joshua P. Taygerly、Lawrence R. McGee、Steven M. Rubenstein、Jonathan B. Houze、Timothy D. Cushing、Yang Li、Alykhan Motani、Jin-Long Chen、Walter Frankmoelle、Guosen Ye、Marc R. Learned、Juan Jaen、Shichang Miao、Pieter B. Timmermans、Martin Thoolen、Patrick Kearney、John Flygare、Holger Beckmann、Jennifer Weiszmann、Michelle Lindstrom、Nigel Walker、Jinsong Liu、Donna Biermann、Zhulun Wang、Atsushi Hagiwara、Tetsuya Iida、Hisateru Aramaki、Yuki Kitao、Hisashi Shinkai、Noboru Furukawa、Jun Nishiu、Motonao Nakamura

  DOI：10.1016/j.bmc.2012.11.058

  日期：2013.2

  PPAR gamma is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPAR gamma modulators (SPPAR gamma Ms) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPAR gamma full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPAR gamma partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs. (C) 2012 Elsevier Ltd. All rights reserved.