ethyl 3-(dimethylamino)-3-(3-thienyl)propionate | 1119825-42-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(dimethylamino)-3-(3-thienyl)propionate
• 英文别名: Ethyl 3-(dimethylamino)-3-thiophen-3-ylpropanoate
• CAS: 1119825-42-1
• 化学式: C₁₁H₁₇NO₂S
• 分子量: 227.327
• InChiKey: RJSANKVLGRFKFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(dimethylamino)-3-(3-thienyl)propionate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以97%的产率得到3-(dimethylamino)-3-thienylpropan-1-ol
  参考文献：
  名称：

  Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists—Structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC)

  摘要：

  Compounds based on the 3-(dimethylamino)butyl dimethylcarbamate (DMABC) scaffold were synthesized and pharmacologically characterized at the alpha(4)beta(2), alpha(3)beta(4), alpha(4)beta(4) and alpha(7) neuronal nicotinic acetylcholine receptors (nAChRs). The carbamate functionality and a small hydrophobic substituent in the C-3 position were found to be vital for the binding affinity to the nAChRs, whereas the carbamate nitrogen substituents were important for nAChR subtype selectivity. Finally, the compounds were found to be agonists at the alpha(3)beta(4) nAChR. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.011
• 作为产物：
  描述：

  ethyl (2E)-3-(3-thienyl)propenoate 在 二甲胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以38%的产率得到ethyl 3-(dimethylamino)-3-(3-thienyl)propionate
  参考文献：
  名称：

  Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists—Structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC)

  摘要：

  Compounds based on the 3-(dimethylamino)butyl dimethylcarbamate (DMABC) scaffold were synthesized and pharmacologically characterized at the alpha(4)beta(2), alpha(3)beta(4), alpha(4)beta(4) and alpha(7) neuronal nicotinic acetylcholine receptors (nAChRs). The carbamate functionality and a small hydrophobic substituent in the C-3 position were found to be vital for the binding affinity to the nAChRs, whereas the carbamate nitrogen substituents were important for nAChR subtype selectivity. Finally, the compounds were found to be agonists at the alpha(3)beta(4) nAChR. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.011

文献信息

• Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists—Structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC)
  作者：Camilla P. Hansen、Anders A. Jensen、Thomas Balle、Klaus Bitsch-Jensen、Mohamud M. Hassan、Tommy Liljefors、Bente Frølund

  DOI：10.1016/j.bmcl.2008.11.011

  日期：2009.1

  Compounds based on the 3-(dimethylamino)butyl dimethylcarbamate (DMABC) scaffold were synthesized and pharmacologically characterized at the alpha(4)beta(2), alpha(3)beta(4), alpha(4)beta(4) and alpha(7) neuronal nicotinic acetylcholine receptors (nAChRs). The carbamate functionality and a small hydrophobic substituent in the C-3 position were found to be vital for the binding affinity to the nAChRs, whereas the carbamate nitrogen substituents were important for nAChR subtype selectivity. Finally, the compounds were found to be agonists at the alpha(3)beta(4) nAChR. (C) 2008 Elsevier Ltd. All rights reserved.