8R-hydroxylobel-9-ene | 758717-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8R-hydroxylobel-9-ene
• 英文别名: (1R)-2-[(2R,6S)-1-methyl-6-[(E)-2-phenylethenyl]piperidin-2-yl]-1-phenylethanol
• CAS: 758717-83-8
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: IKYXUFYHDWVXST-OWHMEISOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8R-hydroxylobel-9-ene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 生成 8R-hydroxylobelane
  参考文献：
  名称：

  Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters

  摘要：

  A series of des-keto lobeline analogs has been synthesized and evaluated for their ability to inhibit the dopamine transporter (DAT) and serotonin transporter (SERT) function and for their affinity for the synaptic vesicle monoamine transporter (VMAT2), as well as for alpha 4 beta 2* and alpha 7* neuronal nicotinic acetylcholine receptors (nAChRs). The enantiomers 8R-hydroxylobel-9-ene (3a) and 10S-hydroxylobel-7-ene (3c) exhibited high potency and selectivity at SERT and DAT, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.070
• 作为产物：
  描述：

  洛贝林 在 sodium tetrahydroborate 、 磷酸 作用下， 以 乙醇 为溶剂， 生成 8R-hydroxylobel-9-ene
  参考文献：
  名称：

  Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters

  摘要：

  A series of des-keto lobeline analogs has been synthesized and evaluated for their ability to inhibit the dopamine transporter (DAT) and serotonin transporter (SERT) function and for their affinity for the synaptic vesicle monoamine transporter (VMAT2), as well as for alpha 4 beta 2* and alpha 7* neuronal nicotinic acetylcholine receptors (nAChRs). The enantiomers 8R-hydroxylobel-9-ene (3a) and 10S-hydroxylobel-7-ene (3c) exhibited high potency and selectivity at SERT and DAT, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.070

文献信息

• US7368443B2
  申请人：——

  公开号：US7368443B2

  公开（公告）日：2008-05-06
• [EN] TREATING PROTEIN MISFOLDING DISEASES<br/>[FR] TRAITEMENT DES PATHOLOGIES DE MAUVAIS REPLIEMENT DES PROTÉINES
  申请人：MAYO FOUNDATION

  公开号：WO2009061906A2

  公开（公告）日：2009-05-14

  This document provides methods and materials related to treating a protein misfolding disease. For example, methods and materials relating to the use of a lobeline compound to treat a protein misfolding disease are provided.
• Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters
  作者：Guangrong Zheng、David B. Horton、Agripina G. Deaciuc、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmcl.2006.07.070

  日期：2006.10

  A series of des-keto lobeline analogs has been synthesized and evaluated for their ability to inhibit the dopamine transporter (DAT) and serotonin transporter (SERT) function and for their affinity for the synaptic vesicle monoamine transporter (VMAT2), as well as for alpha 4 beta 2* and alpha 7* neuronal nicotinic acetylcholine receptors (nAChRs). The enantiomers 8R-hydroxylobel-9-ene (3a) and 10S-hydroxylobel-7-ene (3c) exhibited high potency and selectivity at SERT and DAT, respectively. (c) 2006 Elsevier Ltd. All rights reserved.