11-(3-(4-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-1H-1,2,3-triazol-1-yl)propoxy)-N-propylnoraporphine | 1297273-62-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 11-(3-(4-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-1H-1,2,3-triazol-1-yl)propoxy)-N-propylnoraporphine
• 英文别名: 11-[3-[4-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]triazol-1-yl]propoxy]-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• CAS: 1297273-62-1
• 化学式: C₃₇H₄₆N₆O₂
• 分子量: 606.811
• InChiKey: RXIFDJMCJKEING-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  11-(3-(4-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-1H-1,2,3-triazol-1-yl)propoxy)-N-propylnoraporphine 在 二乙胺 作用下， 以 乙醇 为溶剂， 生成 11-(3-(4-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-1H-1,2,3-triazol-1-yl)propoxy)-N-propylnoraporphine 、 11-(3-(4-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-1H-1,2,3-triazol-1-yl)propoxy)-N-propylnoraporphine
  参考文献：
  名称：

  Further SAR study on 11-O-substituted aporphine analogues: Identification of highly potent dopamine D3 receptor ligands

  摘要：

  A series of new aporphine analogues (aporlogues) were prepared from appropriate aporphine precursors and arylpiperazines using the Click reaction protocol. These compounds displayed good to high affinity at the D-3 receptor, low or no affinity at the D-1 and D-2 receptors. Compounds 7f and 11c stood out as the most potent at the D-3 receptor among our newly synthesized aporlogues with K-i values of 2.67 and 1.14 nM, respectively. Further assay at the 5-HT1A receptor revealed that aporlogues 7f and 11c also showed high affinity at this receptor with K-i values of 9.68 and 7.59 nM, respectively. They were 3.6- and 6.6-fold more potent at the D-3 over 5-HT1A receptors. Such D-3/5-HT1A dual property of these compounds may be useful in the treatment of several brain disorders. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.053
• 作为产物：
  描述：

  (+/-)-11-Hydroxy-N-propylnoraporphine 在 copper(l) iodide 、 sodium azide 、 四丁基溴化铵 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 11-(3-(4-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-1H-1,2,3-triazol-1-yl)propoxy)-N-propylnoraporphine
  参考文献：
  名称：

  Further SAR study on 11-O-substituted aporphine analogues: Identification of highly potent dopamine D3 receptor ligands

  摘要：

  A series of new aporphine analogues (aporlogues) were prepared from appropriate aporphine precursors and arylpiperazines using the Click reaction protocol. These compounds displayed good to high affinity at the D-3 receptor, low or no affinity at the D-1 and D-2 receptors. Compounds 7f and 11c stood out as the most potent at the D-3 receptor among our newly synthesized aporlogues with K-i values of 2.67 and 1.14 nM, respectively. Further assay at the 5-HT1A receptor revealed that aporlogues 7f and 11c also showed high affinity at this receptor with K-i values of 9.68 and 7.59 nM, respectively. They were 3.6- and 6.6-fold more potent at the D-3 over 5-HT1A receptors. Such D-3/5-HT1A dual property of these compounds may be useful in the treatment of several brain disorders. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.053

文献信息

• Further SAR study on 11-O-substituted aporphine analogues: Identification of highly potent dopamine D3 receptor ligands
  作者：Na Ye、QianQian Wu、Liyuan Zhu、Longtai Zheng、Bo Gao、Xuechu Zhen、Ao Zhang

  DOI：10.1016/j.bmc.2011.01.053

  日期：2011.3

  A series of new aporphine analogues (aporlogues) were prepared from appropriate aporphine precursors and arylpiperazines using the Click reaction protocol. These compounds displayed good to high affinity at the D-3 receptor, low or no affinity at the D-1 and D-2 receptors. Compounds 7f and 11c stood out as the most potent at the D-3 receptor among our newly synthesized aporlogues with K-i values of 2.67 and 1.14 nM, respectively. Further assay at the 5-HT1A receptor revealed that aporlogues 7f and 11c also showed high affinity at this receptor with K-i values of 9.68 and 7.59 nM, respectively. They were 3.6- and 6.6-fold more potent at the D-3 over 5-HT1A receptors. Such D-3/5-HT1A dual property of these compounds may be useful in the treatment of several brain disorders. (C) 2011 Elsevier Ltd. All rights reserved.