cis-8-hydroxy-3-(n-propyl)-1,2,3a,4,5,9b-hexahydro-3H-benzindole hydrobromide | 251327-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cis-8-hydroxy-3-(n-propyl)-1,2,3a,4,5,9b-hexahydro-3H-benzindole hydrobromide
• 英文别名: cis-(+/-)-2,3,3a,4,5,9b-hexahydro-8-hydroxy-3-n-propyl-1H-benz[e]indole hydrobromide；cis-8-Hydroxy-3-(n-propyl)-1,2,3a,4,5,9b-hexahydro-1H-benz[e]indole hydrobromide, >=98% (HPLC), solid；(3aR,9bS)-3-propyl-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-8-ol;hydrobromide
• CAS: 251327-24-9
• 化学式: BrH*C₁₅H₂₁NO
• 分子量: 312.25
• InChiKey: UMGQLEXNQCHIFN-NQQJLSKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cis-(+/-)-1,3,3a,4,5,9b-hexahydro-8-methoxy-3-n-propyl-2H-benz[e]indol-2-one 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 cis-8-hydroxy-3-(n-propyl)-1,2,3a,4,5,9b-hexahydro-3H-benzindole hydrobromide
  参考文献：
  名称：

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles: synthesis and evaluation of dopamine D2 and D3 receptor binding affinity

  摘要：

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D-2S and D-3 receptor binding affinity. The tricyclic benz[e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D-3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D-3 receptors was shown by compounds substituted with N-n propyl or N-allyl groups. The cis-(+/-)-N-allyl derivative 21e demonstrated a D-2S /D-3 selectivity of 290. Resolution of cis-(+/-)-5 and trans-(+/-)-21c into individual enantiomers showed that in both series the more active isomer had 3aR absolute configuration. These novel Ligands may be useful tools for gaining additional information about the DA D-3 receptor. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80098-1

文献信息

• cis-1,2,3a,4,5,9b-Hexahydro-3H-benz[e] indoles: Synthesis and In Vitro Binding Affinity at Dopamine D1 and D2 Receptors
  作者：Sharon F. Cruse、Jennifer Lear、Cheryl L. Klein、Peter H. Andersen、Ronald M. Dick、A. Michael Crider

  DOI：10.1002/jps.2600820324

  日期：1993.3

  9b-hexahydro-3H-benz[e]indoles. The stereochemistry was confirmed by single-crystal X-ray analysis. In the 6-hydroxy series, the binding affinity at D1 and D2 receptors was of the order 22 (N-n-butyl) > 21 (N-n-propyl) > 23 (N-H). The compounds demonstrated greater binding affinity at D2 receptors than at D1 binding sites. In contrast, 8-OH derivatives exhibited affinity only for D2 receptors, with 25 (N-n-butyl)

  合成了顺式1,2,3a，4,5,9b-六氢-3H-苯并[e]吲哚并评估了其对多巴胺D1和D2受体的结合亲和力。通过还原对空气敏感的三环烯胺10-14，可以容易地制备目标化合物21-25。用硼氢化钠，氰基硼氢化钠，乙醇中的碳载钯和乙醇或乙酸中的氧化铂还原10-14，仅得到顺式（3a，9b）1,2,3a，4,5,9b-六氢-3H -苯并[e]吲哚。通过单晶X射线分析证实了立体化学。在6-羟基系列中，在D1和D2受体上的结合亲和力为22（Nn-丁基）> 21（Nn-丙基）> 23（NH）。该化合物对D2受体的结合亲和力大于对D1结合位点的结合亲和力。相反，8-OH衍生物仅表现出对D2受体的亲和力，
• Novel D3 Dopamine Receptor Agonists to Treat Dyskinesia in Parkinson's Disease
  申请人：College of Medicine Philadelphia Health & Education Corporation d/b/a Drexel University

  公开号：US20140228355A1

  公开（公告）日：2014-08-14

  The present invention provides a method of inhibiting, suppressing or preventing levodopa-induced dyskinesia in a patient suffering from Parkinson's Disease, comprising the step of administering to the patient a pharmaceutical composition comprising at least one compound of the invention. The present invention further provides a method of inhibiting, suppressing or preventing Parkinson's Disease in a patient, comprising the step of administering to the patient a pharmaceutical composition comprising at least one compound of the invention.

  本发明提供了一种方法，用于抑制、抑制或预防帕金森病患者的左旋多巴诱发的运动障碍，包括向患者给予至少一种本发明化合物的药物组合物。本发明还提供了一种方法，用于抑制、抑制或预防帕金森病患者的病情，包括向患者给予至少一种本发明化合物的药物组合物。
• D3 dopamine receptor agonists to treat dyskinesia in Parkinson's disease
  申请人：DREXEL UNIVERSITY

  公开号：US10543180B2

  公开（公告）日：2020-01-28

  The present invention provides a method of inhibiting, suppressing or preventing levodopa-induced dyskinesia in a patient suffering from Parkinson's Disease, comprising the step of administering to the patient a pharmaceutical composition comprising at least one compound of the invention. The present invention further provides a method of inhibiting, suppressing or preventing Parkinson's Disease in a patient, comprising the step of administering to the patient a pharmaceutical composition comprising at least one compound of the invention.

  本发明提供了一种抑制、抑制或预防帕金森病患者左旋多巴诱发的运动障碍的方法，包括向患者施用包含至少一种本发明化合物的药物组合物的步骤。本发明进一步提供了一种抑制、抑制或预防患者帕金森病的方法，包括向患者施用包含至少一种本发明化合物的药物组合物的步骤。
• NOVEL D3 DOPAMINE RECEPTOR AGONISTS TO TREAT DYSKINESIA IN PARKINSON'S DISEASE
  申请人：Philadelphia Health and Education Corporation

  公开号：EP2603215A2

  公开（公告）日：2013-06-19
• US9289400B2
  申请人：——

  公开号：US9289400B2

  公开（公告）日：2016-03-22