(1S,2S,3R,6S)-9-[1-[2,3']Bithiophenyl-5-yl-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]decane-2-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: (1S,2S,3R,6S)-9-[1-[2,3']Bithiophenyl-5-yl-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]decane-2-carboxylic acid methyl ester
• 英文别名: methyl (1S,2S,3R,6S,9Z)-9-[(5-thiophen-3-ylthiophen-2-yl)methylidene]-7-azatricyclo[4.3.1.03,7]decane-2-carboxylate
• 化学式: C₂₀H₂₁NO₂S₂
• 分子量: 371.524
• InChiKey: CBNNPWOODQAMIN-HFYXDYEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,3R,6S)-(Z)-9-[(tri-n-butylstannyl)methylene]-7-azatricyclo[4.3.1.0^3,7]decane-2β-carboxylic acid methyl ester 在 palladium diacetate 、 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2S,3R,6S)-9-[1-[2,3']Bithiophenyl-5-yl-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]decane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Discovery of novel conformationally constrained tropane-based biaryl and arylacetylene ligands as potent and selective norepinephrine transporter inhibitors and potential antidepressants

  摘要：

  To further explore the structure-activity relationships of conformationally constrained tropanes, a number of new biaryl and arylacetylene analogs were designed and synthesized. Some of these compounds such as 3a-b, 3d, 3f-h, 5b, and 7g were found to be highly potent and selective or mixed norepinephrine transporter (NET) inhibitors with K-i values of 0.8-9.4 nM. Moreover, all of these compounds display weak to extremely weak muscarinic receptor binding affinity, indicating that as potential antidepressants, they may overcome certain side effects that are of concern with other antidepressants, which are thought to be mediated by their anticholinergic properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.083

文献信息

• Discovery of novel conformationally constrained tropane-based biaryl and arylacetylene ligands as potent and selective norepinephrine transporter inhibitors and potential antidepressants
  作者：Jia Zhou、Thomas Kläß、Kenneth M. Johnson、Kelly M. Giberson、Alan P. Kozikowski

  DOI：10.1016/j.bmcl.2005.03.083

  日期：2005.5

  To further explore the structure-activity relationships of conformationally constrained tropanes, a number of new biaryl and arylacetylene analogs were designed and synthesized. Some of these compounds such as 3a-b, 3d, 3f-h, 5b, and 7g were found to be highly potent and selective or mixed norepinephrine transporter (NET) inhibitors with K-i values of 0.8-9.4 nM. Moreover, all of these compounds display weak to extremely weak muscarinic receptor binding affinity, indicating that as potential antidepressants, they may overcome certain side effects that are of concern with other antidepressants, which are thought to be mediated by their anticholinergic properties. (c) 2005 Elsevier Ltd. All rights reserved.