cis-(-)-2,3,3a,4,5,9b-hexahydro-8-hydroxy-3-n-propyl-1H-benz[e]indole | 147678-60-2

• 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-(-)-2,3,3a,4,5,9b-hexahydro-8-hydroxy-3-n-propyl-1H-benz[e]indole
• 英文别名: rel-(3aR,9bS)-2,3,3a,4,5,9b-Hexahydro-3-propyl-1H-benz[e]indol-8-ol；(3aR,9bS)-3-propyl-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-8-ol
• CAS: 147678-60-2
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: LJDRQPOQHHOXHM-DZGCQCFKSA-N

物化性质

• 沸点：
  365.1±42.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

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：

  cis-8-hydroxy-3-(n-propyl)1,2,3a,4,5,9b-hexahydro-1H-benz[e]indole hydrochloride 在 CHIRALCEL OD 、 二乙胺 作用下， 以 正庚烷 、 异丙醇 为溶剂， 以43 mg的产率得到cis-(+)-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

• ENANTIOMERS OF CIS-BENZ E]INDOLE COMPOUNDS, THEIR PREPARATION AND UTILITY AS DOPAMINE-D3 RECEPTOR SELECTIVE AGENTS
  申请人：NOVO NORDISK A/S

  公开号：EP0861234A1

  公开（公告）日：1998-09-02
• [EN] ENANTIOMERS OF CIS-BENZ[E]INDOLE COMPOUNDS, THEIR PREPARATION AND UTILITY AS DOPAMINE-D3 RECEPTOR SELECTIVE AGENTS<br/>[FR] ENANTIOMERES DE COMPOSES DE CIS-BENZ[E]INDOLE, LEUR PREPARATION ET UTILITE EN TANT QU'AGENTS SELECTIFS DU RECEPTEUR DE LA DOPAMINE-D3
  申请人：NOVO NORDISK A/S

  公开号：WO1997017326A1

  公开（公告）日：1997-05-15

  (EN) Enantiomers of cis-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; and 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) Cette invention concerne des énantiomères de composés de cis-Benz[e]indole, représentés par la formule générale (I), dans laquelle R1 est hydrogène, alkyle-C1-6, cycloalkylméthyle, allyle ou alcényle, R4 est hydroxy, alkoxy-C1-6, O-acyle, triflate ou carbamyle, et R2, R3, et R5 sont identiques ou différents et représentent indépendamment hydrogène, halogène trifluorométhyle ou alkyle-C1-6. Lesdits énantiomères s'avèrent utiles en tant que ligands sélectifs du récepteur de la dopamine-D3 dans le traitement des troubles du système nerveux central liés à un dysfonctionnement du système central de la dopamine.