cis-syn-6,7-dimethoxy-1-methyl-1,3,3a,4,5,9a-hexahydro-2H-benzindol-2-ene

• 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-syn-6,7-dimethoxy-1-methyl-1,3,3a,4,5,9a-hexahydro-2H-benzindol-2-ene
• 英文别名: (1S,3aR,9bS)-6,7-dimethoxy-1-methyl-1,3,3a,4,5,9b-hexahydrobenzo[e]indol-2-one
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: VDEPXGKBILDZRM-KDDOJWQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-syn-6,7-dimethoxy-1-methyl-1,3,3a,4,5,9a-hexahydro-2H-benzindol-2-ene 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (1S,3aR,9bS)-6,7-dimethoxy-1-methyl-3-propyl-1,2,3a,4,5,9b-hexahydrobenzo[e]indole
  参考文献：
  名称：

  Synthesis and evaluation of cis-1-methyl-3-n-propyl-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indoles for in vitro dopamine D1 and D2 receptor binding affinity

  摘要：

  cis-syn-1-Methyl-3-n-propyl-2,3,3a,4,5,9b-hexahydro-1H-benz[e] 6 and 7 were synthesized as conformationally rigid analogs of 4-methyl-3-(3,4-dihydroxyphenyl)-1-(n-propyl)pyrrolidine 1 and evaluated for dopamine D-1 and D-2 receptor binding affinity. The target compounds 6 and 7 were obtained from the key tricyclic lactams 10 and 11, respectively. The stereochemistry was confirmed by single crystal X-ray analysis. Compounds 6 and 7 demonstrated low in vitro binding affinity at D-1 and D-2 receptors using [H-3]SCH 23390 and [3H]spiperone as the D-1 and D-2 receptor radioligands, respectively. These data suggest that the 1-methyl group may interfere with the binding of 6 and 7 at D, and D,receptors. Molecular modeling studies revealed that unlike the 4-methyl group of 1, the 1-methyl group of 6 and 7 was directed toward the so-called 'steric occlusion site' of the dopamine receptor.

  DOI：

  10.1016/0223-5234(96)88313-9
• 作为产物：
  描述：

  5,6-二甲氧基-1,2,3,4-四氢萘-2-酮 在 palladium on activated charcoal 四氢吡咯 、 水 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 cis-syn-6,7-dimethoxy-1-methyl-1,3,3a,4,5,9a-hexahydro-2H-benzindol-2-ene
  参考文献：
  名称：

  Synthesis and evaluation of cis-1-methyl-3-n-propyl-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indoles for in vitro dopamine D1 and D2 receptor binding affinity

  摘要：

  cis-syn-1-Methyl-3-n-propyl-2,3,3a,4,5,9b-hexahydro-1H-benz[e] 6 and 7 were synthesized as conformationally rigid analogs of 4-methyl-3-(3,4-dihydroxyphenyl)-1-(n-propyl)pyrrolidine 1 and evaluated for dopamine D-1 and D-2 receptor binding affinity. The target compounds 6 and 7 were obtained from the key tricyclic lactams 10 and 11, respectively. The stereochemistry was confirmed by single crystal X-ray analysis. Compounds 6 and 7 demonstrated low in vitro binding affinity at D-1 and D-2 receptors using [H-3]SCH 23390 and [3H]spiperone as the D-1 and D-2 receptor radioligands, respectively. These data suggest that the 1-methyl group may interfere with the binding of 6 and 7 at D, and D,receptors. Molecular modeling studies revealed that unlike the 4-methyl group of 1, the 1-methyl group of 6 and 7 was directed toward the so-called 'steric occlusion site' of the dopamine receptor.

  DOI：

  10.1016/0223-5234(96)88313-9