(S)-N-(2-methoxy-5-(pyridin-4-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyrimidin-2-yl)cyclopropylamino)propanamide | 1240523-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-(2-methoxy-5-(pyridin-4-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyrimidin-2-yl)cyclopropylamino)propanamide
• 英文别名: (2S)-N-(2-methoxy-5-pyridin-4-ylpyridin-3-yl)-3-phenyl-2-[(1-pyrimidin-2-ylcyclopropyl)amino]propanamide
• CAS: 1240523-32-3
• 化学式: C₂₇H₂₆N₆O₂
• 分子量: 466.542
• InChiKey: NGCYGJISKHAYBI-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-methoxy-5-(pyridin-4-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyrimidin-2-yl)cyclopropylamino)propanamide 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 (2S)-N-(2-oxo-5-pyridin-4-yl-1H-pyridin-3-yl)-3-phenyl-2-[(1-pyrimidin-2-ylcyclopropyl)amino]propanamide
  参考文献：
  名称：

  Phenylalanine derivatives as GPR142 agonists for the treatment of Type II diabetes

  摘要：

  GPR142 is a novel GPCR that is predominantly expressed in pancreatic beta-cells. GPR142 agonists potentiate glucose-dependent insulin secretion, and therefore can reduce the risk of hypoglycemia. Optimization of our lead pyridinone-phenylalanine series led to a proof-of-concept compound 22, which showed in vivo efficacy in mice with dose-dependent increase in insulin secretion and a decrease in glucose levels. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.015
• 作为产物：
  描述：

  3-氨基-5-溴-2-甲氧基吡啶 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 3.0h， 生成 (S)-N-(2-methoxy-5-(pyridin-4-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyrimidin-2-yl)cyclopropylamino)propanamide
  参考文献：
  名称：

  Phenylalanine derivatives as GPR142 agonists for the treatment of Type II diabetes

  摘要：

  GPR142 is a novel GPCR that is predominantly expressed in pancreatic beta-cells. GPR142 agonists potentiate glucose-dependent insulin secretion, and therefore can reduce the risk of hypoglycemia. Optimization of our lead pyridinone-phenylalanine series led to a proof-of-concept compound 22, which showed in vivo efficacy in mice with dose-dependent increase in insulin secretion and a decrease in glucose levels. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.015

文献信息

• PHENYLANALINE AMIDE DERIVATIVES USEFUL FOR TREATING INSULIN-RELATED DISEASES AND CONDITIONS
  申请人：Du Xiaohui

  公开号：US20120115811A1

  公开（公告）日：2012-05-10

  Provided herein are compounds of formula I: wherein A, B, X, R 1 , R 2 and subscript n are as defined in the following disclosure. Compositions comprising the compounds are also provided, as well as methods for their use, for example, in treatment of type 2 diabetes and type 2 diabetes-related conditions.

  本文所提供的是I式化合物：其中A、B、X、R1、R2和下标n如下所述。本文还提供了包含该化合物的组合物，以及使用它们的方法，例如用于治疗2型糖尿病和2型糖尿病相关疾病的方法。
• US8785468B2
  申请人：——

  公开号：US8785468B2

  公开（公告）日：2014-07-22
• Phenylalanine derivatives as GPR142 agonists for the treatment of Type II diabetes
  作者：Xiaohui Du、Yong-Jae Kim、SuJen Lai、Xi Chen、Mike Lizarzaburu、Simon Turcotte、Zice Fu、Qingxiang Liu、Ying Zhang、Alykhan Motani、Kozo Oda、Ryo Okuyama、Futoshi Nara、Michiko Murakoshi、Angela Fu、Jeff D. Reagan、Peter Fan、Yumei Xiong、Wang Shen、Leping Li、Jonathan Houze、Julio C. Medina

  DOI：10.1016/j.bmcl.2012.08.015

  日期：2012.10

  GPR142 is a novel GPCR that is predominantly expressed in pancreatic beta-cells. GPR142 agonists potentiate glucose-dependent insulin secretion, and therefore can reduce the risk of hypoglycemia. Optimization of our lead pyridinone-phenylalanine series led to a proof-of-concept compound 22, which showed in vivo efficacy in mice with dose-dependent increase in insulin secretion and a decrease in glucose levels. (C) 2012 Elsevier Ltd. All rights reserved.