6-methoxy-1-methyl-1,3,4,5-tetrahydro-2H-benzindol-2-ene | 174227-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxy-1-methyl-1,3,4,5-tetrahydro-2H-benzindol-2-ene
• 英文别名: 6-Methoxy-1-methyl-1,3,4,5-tetrahydrobenzo[e]indol-2-one
• CAS: 174227-89-5
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: CZQBQOYKAZTOFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-1-methyl-1,3,4,5-tetrahydro-2H-benzindol-2-ene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以78%的产率得到cis-syn-6-methoxy-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
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 、 2-溴丙酰胺 在 四氢吡咯 、 水 、 对甲苯磺酸 作用下， 生成 6-methoxy-1-methyl-1,3,4,5-tetrahydro-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

文献信息

• 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
  作者：D Ghosh、C.L. Klein、B Garner、P.H. Andersen、A.M. Crider

  DOI：10.1016/0223-5234(96)88313-9

  日期：——

  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.