trans-(-)-2,3,3a,4,5,9b-hexahydro-8-hydroxy-3-n-propyl-1H-benz[e]indole

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-(-)-2,3,3a,4,5,9b-hexahydro-8-hydroxy-3-n-propyl-1H-benz[e]indole
• 英文别名: (3aS,9bS)-3-propyl-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-8-ol
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: LJDRQPOQHHOXHM-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 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：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trans-(+/-)-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， 生成 trans-(-)-2,3,3a,4,5,9b-hexahydro-8-hydroxy-3-n-propyl-1H-benz[e]indole
  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

• [EN] ENANTIOMERS OF TRANS-BENZ[E]INDOLE COMPOUNDS, THEIR PREPARATION AND UTILITY AS DOPAMINE-D3 RECEPTOR SELECTIVE AGENTS<br/>[FR] ENANTIOMERES DE COMPOSES TRANS-BENZ(E)INDOLE, LEUR PREPARATION ET LEUR UTILISATION EN TANT QU'AGENTS SELECTIFS DU RECEPTEUR DOPAMINERGIQUE D3
  申请人：NOVO NORDISK A/S

  公开号：WO1997041101A1

  公开（公告）日：1997-11-06

  (EN) Enantiomers of trans-benz[e]indole compounds of formula (I) wherein R1 is hydrogen, C1-6-alkyl, cycloalkylmethyl, allyl or alkenyl; R4 is hydroxy, C1-6-alkoxy, O-acyl, triflate, or carbamoyl; R2, R3, R5 are the same or different and independently are hydrogen, halogen, trifluoromethyl or C1-6-alkyl, are useful as selective dopamine-D3 receptor ligands in the treatment of central nervous system ailments related to dysfunction of the central dopamine system.(FR) On décrit des énantiomères de composés trans-benz(e)indole de la formule (I) dans laquelle R1 représente hydrogène, alkyle C1-6, cycloalkylméthyle, allyle ou alcényle, R4 représente hydroxy, alcoxy C1-6, O-acyle, triflate ou carbamoyle, R2, R3 et R5 sont semblables ou différents et représentent indépendamment hydrogène, halogène, trifluorométhyle ou alkyle C1-6. Ces composés sont utiles en tant que ligands du récepteur dopaminergique D3, dans le traitement d'affections du système nerveux central associées à une dysfonction du système dopaminergique central.
• 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
  作者：Xiaodong Song、A.Michael Crider、Sharon F. Cruse、Debasis Ghosh、Cheryl Klein-Stevens、Li Liang、Mark A. Scheideler、Annemarie Varming、Inger Søtofte

  DOI：10.1016/s0223-5234(99)80098-1

  日期：1999.6

  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.