2-((1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)isoindoline-1,3-dione | 1007116-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)isoindoline-1,3-dione
• CAS: 1007116-71-3
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: GCRZQSUFHMMSKT-JGPRNRPPSA-N

物化性质

• 沸点：
  405.5±38.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-((1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)isoindoline-1,3-dione 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(1S,3S,5R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives

  摘要：

  The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine with an exo-tropanyl unit led to the identification of compound 15 which provides a combination of excellent potency against human and murine receptors, drug-like properties and pharmacokinetics, thus providing a valuable tool for the evaluation of CXCR3 antagonists in models of human disease. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.109
• 作为产物：
  描述：

  2-((1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)isoindoline-1,3-dione 在 1-氯乙基氯甲酸酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以87%的产率得到2-((1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives

  摘要：

  The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine with an exo-tropanyl unit led to the identification of compound 15 which provides a combination of excellent potency against human and murine receptors, drug-like properties and pharmacokinetics, thus providing a valuable tool for the evaluation of CXCR3 antagonists in models of human disease. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.109

文献信息

• Development of CXCR3 antagonists. Part 4: Discovery of 2-amino-(4-tropinyl)quinolines
  作者：Roland L. Knight、Daniel R. Allen、Helen L. Birch、Gayle A. Chapman、Frances C. Galvin、Louise A. Jopling、Christopher J. Lock、Johannes W.G. Meissner、David A. Owen、Gilles Raphy、Robert J. Watson、Sophie C. Williams

  DOI：10.1016/j.bmcl.2007.11.075

  日期：2008.1

  The synthesis and biological evaluation of a novel series of 2-aminoquinoline substituted piperidines and tropanes incorporating a homotropene moiety is herein described. The series exhibits potent antagonism of the CXCR3 receptor and superior physicochemical properties. Compound 24d was found to be orally bioavailable, and PK/PD studies suggested it as a suitable tool for studying the role of CXCR3 in models of disease. (c) 2007 Elsevier Ltd. All rights reserved.