1,2-methano-7-methoxy-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine | 151793-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2-methano-7-methoxy-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine
• 英文别名: 6-methoxy-N,N-dipropyl-1,2,3,7b-tetrahydrocyclopropa[a]naphthalen-1a-amine
• CAS: 151793-13-4
• 化学式: C₁₈H₂₇NO
• 分子量: 273.418
• InChiKey: KCYWMIBKMYGBCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-methano-7-methoxy-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine 在 氢溴酸 作用下， 反应 2.0h， 生成 7-(dipropylamino)-7,8-methano-5,6,7,8-tetrahydronaphth-2-ol
  参考文献：
  名称：

  Phenolic derivatives of 1,2-methano-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine. Structural hybrids of 2-aminotetralin- and phenylcyclopropylamine-derived 5-HT1A-receptor agonists

  摘要：

  Three phenolic derivatives of 1,2-methano-N,N-dipropyl- 1,2,3,4-tetrahydronaphth-2-ylamine 6-8 were synthesized as structural hybrids of the potent 5-HT1A-receptor agonist 8-OH-DPAT 1 and 2 related phenolic phenylcyclopropylamines 4 and 5. The new compounds were assayed for 5-HT1A-receptor affinity and efficacy in vitro. Hybrids 6 and 7 were considered to be inactive but 8 had a K(i) value of 130 nM for [H-3]-8-OH-DPAT labelled 5-HT1A-receptors and produced an inhibition of the cAMP-production in the VIP-stimulated adenylyl cyclase assay. Thus, 8 is able to bind to and stimulate 5-HT1A-receptors. The results are discussed in relation to a previously described 3-D model for 5-HT1A-receptor agonists.

  DOI：

  10.1016/0223-5234(93)90126-y
• 作为产物：
  描述：

  7-甲氧基-2-萘满酮 在 diethylzinc 、 对甲苯磺酸 作用下， 以 正己烷 、 正戊烷 、 苯 为溶剂， 反应 145.0h， 生成 1,2-methano-7-methoxy-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine
  参考文献：
  名称：

  Phenolic derivatives of 1,2-methano-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine. Structural hybrids of 2-aminotetralin- and phenylcyclopropylamine-derived 5-HT1A-receptor agonists

  摘要：

  Three phenolic derivatives of 1,2-methano-N,N-dipropyl- 1,2,3,4-tetrahydronaphth-2-ylamine 6-8 were synthesized as structural hybrids of the potent 5-HT1A-receptor agonist 8-OH-DPAT 1 and 2 related phenolic phenylcyclopropylamines 4 and 5. The new compounds were assayed for 5-HT1A-receptor affinity and efficacy in vitro. Hybrids 6 and 7 were considered to be inactive but 8 had a K(i) value of 130 nM for [H-3]-8-OH-DPAT labelled 5-HT1A-receptors and produced an inhibition of the cAMP-production in the VIP-stimulated adenylyl cyclase assay. Thus, 8 is able to bind to and stimulate 5-HT1A-receptors. The results are discussed in relation to a previously described 3-D model for 5-HT1A-receptor agonists.

  DOI：

  10.1016/0223-5234(93)90126-y

文献信息

• Phenolic derivatives of 1,2-methano-N,N-dipropyl-1,2,3,4-tetrahydronaphth-2-ylamine. Structural hybrids of 2-aminotetralin- and phenylcyclopropylamine-derived 5-HT1A-receptor agonists
  作者：J Vallgårda、LE Arvidsson、BE Svensson、CJ Fowler、U Hacksell

  DOI：10.1016/0223-5234(93)90126-y

  日期：1993.1

  Three phenolic derivatives of 1,2-methano-N,N-dipropyl- 1,2,3,4-tetrahydronaphth-2-ylamine 6-8 were synthesized as structural hybrids of the potent 5-HT1A-receptor agonist 8-OH-DPAT 1 and 2 related phenolic phenylcyclopropylamines 4 and 5. The new compounds were assayed for 5-HT1A-receptor affinity and efficacy in vitro. Hybrids 6 and 7 were considered to be inactive but 8 had a K(i) value of 130 nM for [H-3]-8-OH-DPAT labelled 5-HT1A-receptors and produced an inhibition of the cAMP-production in the VIP-stimulated adenylyl cyclase assay. Thus, 8 is able to bind to and stimulate 5-HT1A-receptors. The results are discussed in relation to a previously described 3-D model for 5-HT1A-receptor agonists.