N-benzyl-N,N',N'-trimethyl-(1R,2R)-cyclohexane-1,2-diamine | 67198-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N,N',N'-trimethyl-(1R,2R)-cyclohexane-1,2-diamine
• 英文别名: (1R,2R)-2-N-benzyl-1-N,1-N,2-N-trimethylcyclohexane-1,2-diamine
• CAS: 67198-28-1；79150-47-3
• 化学式: C₁₆H₂₆N₂
• 分子量: 246.396
• InChiKey: YIPKZGXFIFMNAA-HZPDHXFCSA-N

物化性质

• 沸点：
  335.0±35.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-N,N',N'-trimethyl-(1R,2R)-cyclohexane-1,2-diamine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到(1R,2R)-N,N,N’-三甲基-1,2-环己二胺
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of pirenzepine analogs bearing a 1,2-cyclohexanediamine and perhydroquinoxaline units in exchange for the piperazine ring as antimuscarinics

  摘要：

  Pirenzepine (2) is one of the most selective muscarinic M-1 versus M-2 receptor antagonists known. A series of 2 analogs, in which the piperazyl moiety was replaced by a cis-and trans-cyclohexane-1,2-diamine (3-6) or a trans-and cis-perhydroquinoxaline rings (7 and 8) were prepared, with the aim to investigate the role of the piperazine ring of 2 in the interaction with the muscarinic receptors. The structural change leading to compounds 3-6 abolished in binding assays the muscarinic M-1/M-2 selectivity of 2, due to an increased M-2 affinity. Rather, compounds 3-6 displayed a reversed selectivity showing more affinity at the muscarinic M-2 receptor than at all the other subtypes tested. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.025
• 作为产物：
  描述：

  聚合甲醛 、 (1R,2R)-N1-苄基环己烷-1,2-二胺 在 甲酸 作用下， 以 水 为溶剂， 反应 12.0h， 以73%的产率得到N-benzyl-N,N',N'-trimethyl-(1R,2R)-cyclohexane-1,2-diamine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of pirenzepine analogs bearing a 1,2-cyclohexanediamine and perhydroquinoxaline units in exchange for the piperazine ring as antimuscarinics

  摘要：

  Pirenzepine (2) is one of the most selective muscarinic M-1 versus M-2 receptor antagonists known. A series of 2 analogs, in which the piperazyl moiety was replaced by a cis-and trans-cyclohexane-1,2-diamine (3-6) or a trans-and cis-perhydroquinoxaline rings (7 and 8) were prepared, with the aim to investigate the role of the piperazine ring of 2 in the interaction with the muscarinic receptors. The structural change leading to compounds 3-6 abolished in binding assays the muscarinic M-1/M-2 selectivity of 2, due to an increased M-2 affinity. Rather, compounds 3-6 displayed a reversed selectivity showing more affinity at the muscarinic M-2 receptor than at all the other subtypes tested. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.025

文献信息

• Design, synthesis, and biological evaluation of pirenzepine analogs bearing a 1,2-cyclohexanediamine and perhydroquinoxaline units in exchange for the piperazine ring as antimuscarinics
  作者：Anna Minarini、Gabriella Marucci、Cristina Bellucci、Gianluca Giorgi、Vincenzo Tumiatti、Maria Laura Bolognesi、Riccardo Matera、Michela Rosini、Carlo Melchiorre

  DOI：10.1016/j.bmc.2008.06.025

  日期：2008.8

  Pirenzepine (2) is one of the most selective muscarinic M-1 versus M-2 receptor antagonists known. A series of 2 analogs, in which the piperazyl moiety was replaced by a cis-and trans-cyclohexane-1,2-diamine (3-6) or a trans-and cis-perhydroquinoxaline rings (7 and 8) were prepared, with the aim to investigate the role of the piperazine ring of 2 in the interaction with the muscarinic receptors. The structural change leading to compounds 3-6 abolished in binding assays the muscarinic M-1/M-2 selectivity of 2, due to an increased M-2 affinity. Rather, compounds 3-6 displayed a reversed selectivity showing more affinity at the muscarinic M-2 receptor than at all the other subtypes tested. (C) 2008 Elsevier Ltd. All rights reserved.