(1S,2S,3R,6S)-9-[3-Trimethylsilanyl-prop-2-yn-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]decane-2-carboxylic acid methyl ester | 854764-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2S,3R,6S)-9-[3-Trimethylsilanyl-prop-2-yn-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]decane-2-carboxylic acid methyl ester
• 英文别名: (1S,2S,3R,6S)-9-[3-Trimethylsilanyl-prop-2-yn-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]decane-2-carboxylic acid methyl ester
• CAS: 854764-69-5
• 化学式: C₁₇H₂₅NO₂Si
• 分子量: 303.476
• InChiKey: FBJLSOKSHVTQSZ-XQPWOCIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,6S)-9-[3-Trimethylsilanyl-prop-2-yn-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]decane-2-carboxylic acid methyl ester 、 1,2-二氟-4-碘代苯 在 四丁基氟化铵 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 生成 (1S,2S,3R,6S)-9-[3-(3,4-Difluoro-phenyl)-prop-2-yn-(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
• 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 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (1S,2S,3R,6S)-9-[3-Trimethylsilanyl-prop-2-yn-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]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