(1S,3S,4R,8R)-3-(4-Bromo-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decane | 910252-42-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1S,3S,4R,8R)-3-(4-Bromo-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decane
• CAS: 910252-42-5
• 化学式: C₁₆H₁₈BrN
• 分子量: 304.23
• InChiKey: KVHKGSIWONIENO-JJXSEGSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R,8R)-3-(4-Bromo-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decane 在 四(三苯基膦)钯 、 六正丁基二锡 、 碘 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of front bridged tricyclic 3β-(4′-halo or 4′-methyl)phenyltropanes bearing methylene or carbomethoxymethylene on the bridge to the 2β-position

  摘要：

  A series of front bridged tricyclic 3 beta-(4'-halo or 4'-methyl)phenyltropanes bearing methylene or carbomethoxymethylene on the bridge to the 2 beta-position was synthesized, and their binding affinities were deter-mined in cells transfected to express human norepinephrine transporter (NET), serotonin transporter (SERT), and dopamine transporter (DAT) via competition binding assays. All compounds studied in this series exhibit a moderate to high potency at all three transporters with SERT or DAT selectivity. 3 beta-(4'-iodo)phenyltropane bearing methylene on the bridge to the 2 beta-position (24) presents a particularly attractive pharmacological profile, with very high SERT affinity (K-i = 0.09 nM) and selectivity versus NET (65-fold) and DAT (94-fold). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.098
• 作为产物：
  描述：

  (1R,2S,3S,5S)-3-(4-Bromo-phenyl)-8-ethoxycarbonylmethyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (1S,3S,4R,8R)-3-(4-Bromo-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decane
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of front bridged tricyclic 3β-(4′-halo or 4′-methyl)phenyltropanes bearing methylene or carbomethoxymethylene on the bridge to the 2β-position

  摘要：

  A series of front bridged tricyclic 3 beta-(4'-halo or 4'-methyl)phenyltropanes bearing methylene or carbomethoxymethylene on the bridge to the 2 beta-position was synthesized, and their binding affinities were deter-mined in cells transfected to express human norepinephrine transporter (NET), serotonin transporter (SERT), and dopamine transporter (DAT) via competition binding assays. All compounds studied in this series exhibit a moderate to high potency at all three transporters with SERT or DAT selectivity. 3 beta-(4'-iodo)phenyltropane bearing methylene on the bridge to the 2 beta-position (24) presents a particularly attractive pharmacological profile, with very high SERT affinity (K-i = 0.09 nM) and selectivity versus NET (65-fold) and DAT (94-fold). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.098