1-phenyl-N3-(3-phenylpropyl)propane-1,3-diamine | 1567843-69-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-phenyl-N3-(3-phenylpropyl)propane-1,3-diamine
• CAS: 1567843-69-9
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: CKUPBJLIFULSFK-UHFFFAOYSA-N

物化性质

• 沸点：
  417.6±40.0 °C(predicted)
• 密度：
  1.023±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.05
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  溴化氰 、 1-phenyl-N3-(3-phenylpropyl)propane-1,3-diamine 以 乙醇 、 二氯甲烷 为溶剂， 以40%的产率得到4-phenyl-1-(3-phenylpropyl)-5,6-dihydro-4H-pyrimidin-2-amine;hydrochloride
  参考文献：
  名称：

  The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships

  摘要：

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.021
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 、 diborane(6) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 1-phenyl-N3-(3-phenylpropyl)propane-1,3-diamine
  参考文献：
  名称：

  The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships

  摘要：

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.021