N-[(1S,2R)-2-((2-[(4-chlorophenyl)carbonyl]amino-6-methylquinazolin-4-yl)amino)cyclohexyl]-N',N"-bis(tert-butoxycarbonyl)guanidine | 1123685-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[(1S,2R)-2-((2-[(4-chlorophenyl)carbonyl]amino-6-methylquinazolin-4-yl)amino)cyclohexyl]-N',N"-bis(tert-butoxycarbonyl)guanidine
• CAS: 1123685-31-3
• 化学式: C₃₃H₄₂ClN₇O₅
• 分子量: 652.193
• InChiKey: GKLJUOVKIWQSMV-RPBOFIJWSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  46.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  155.93
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-[(1S,2R)-2-((2-[(4-chlorophenyl)carbonyl]amino-6-methylquinazolin-4-yl)amino)cyclohexyl]-N',N"-bis(tert-butoxycarbonyl)guanidine 在 盐酸 、 甲醇 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 24.0h， 以54.9%的产率得到N-[(1RS,2SR)-2-((2-[(4-chlorophenyl)carbonyl]amino-6-methylquinazolin-4-yl)amino)cyclohexyl]guanidine dihydrochloride
  参考文献：
  名称：

  Discovery and structure–activity relationships of 4-aminoquinazoline derivatives, a novel class of opioid receptor like-1 (ORL1) antagonists

  摘要：

  Synthesis and structure-activity relationship studies of a series of 4-aminoquinazoline derivatives led to the identification of (1R, 2S)-17, N-[(1R, 2S)-2-({2-[(4-chlorophenyl) carbonyl] amino-6-methylquinazolin-4-yl} amino) cyclohexyl] guanidine dihydrochloride, as a highly potent ORL1 antagonist with up to 3000-fold selectivity over the mu, delta, and kappa opioid receptors. Molecular modeling clarified the structural factors contributing to the high affinity and selectivity of (1R, 2S)-17. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.012
• 作为产物：
  描述：

  4-氯苯甲酰氯 、 N-((1RS,2SR)-2-[(2-amino-6-methylquinazolin-4-yl)-amino]cyclohexyl)-N',N''-bis(tert-butoxycarbonyl)guanidine 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以89%的产率得到N-[(1S,2R)-2-((2-[(4-chlorophenyl)carbonyl]amino-6-methylquinazolin-4-yl)amino)cyclohexyl]-N',N"-bis(tert-butoxycarbonyl)guanidine
  参考文献：
  名称：

  Discovery and structure–activity relationships of 4-aminoquinazoline derivatives, a novel class of opioid receptor like-1 (ORL1) antagonists

  摘要：

  Synthesis and structure-activity relationship studies of a series of 4-aminoquinazoline derivatives led to the identification of (1R, 2S)-17, N-[(1R, 2S)-2-({2-[(4-chlorophenyl) carbonyl] amino-6-methylquinazolin-4-yl} amino) cyclohexyl] guanidine dihydrochloride, as a highly potent ORL1 antagonist with up to 3000-fold selectivity over the mu, delta, and kappa opioid receptors. Molecular modeling clarified the structural factors contributing to the high affinity and selectivity of (1R, 2S)-17. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.012