(1S,3S,4S,8R)-3-(4-chlorophenyl)-7-azatricyclo[5.3.0.04,8]decan-5-one | 190326-85-3

• 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,4S,8R)-3-(4-chlorophenyl)-7-azatricyclo[5.3.0.04,8]decan-5-one
• CAS: 190326-85-3
• 化学式: C₁₅H₁₆ClNO
• 分子量: 261.751
• InChiKey: YNPWRWMCSMUGCA-JLNYLFASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,8R)-3-(4-chlorophenyl)-7-azatricyclo[5.3.0.04,8]decan-5-one 、 膦酰基乙酸甲酯二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 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：

  甲基(1R)-3-(4-氯苯基)-8-甲基-8-氮杂双环[3.2.1]辛烷-2-羧酸酯 在 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 (1S,3S,4S,8R)-3-(4-chlorophenyl)-7-azatricyclo[5.3.0.04,8]decan-5-one
  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

文献信息

• Tropane derivatives having dopamine reuptake inhibitor activity for the treatment of ischemic diseases
  申请人：Scheel-Kruger Jorgen

  公开号：US20050020621A1

  公开（公告）日：2005-01-27

  The present invention relates to the use of tropane derivatives having dopamine reuptake inhibitor activity for the treatment of diseases associated with reduced blood flow to the brain or with instances of a temporary break in blood supply to the brain, such as ischemic diseases.

  本发明涉及使用具有多巴胺再摄取抑制活性的托烷衍生物治疗与脑血流量减少或脑供血暂时中断有关的疾病，如缺血性疾病。
• FUSED TROPANE-DERIVATIVES AS NEUROTRANSMITTER REUPTAKE INHIBITORS
  申请人：NEUROSEARCH A/S

  公开号：EP0858461B1

  公开（公告）日：2002-09-18
• TROPANE DERIVATIVES HAVING DOPAMINE REUPTAKE INHIBITOR ACTIVITY FOR THE TREATMENT OF ISCHEMIC DISEASES
  申请人：NEUROSEARCH A/S

  公开号：EP1453511B1

  公开（公告）日：2006-11-15
• US7381733B2
  申请人：——

  公开号：US7381733B2

  公开（公告）日：2008-06-03
• 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
  作者：Fanxing Zeng、Nachwa Jarkas、Michael J. Owens、Clinton D. Kilts、Charles B. Nemeroff、Mark M. Goodman

  DOI：10.1016/j.bmcl.2006.05.098

  日期：2006.9

  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.