2-(1-苯基-3,4-二氢-1H-异喹啉-2-基)-乙醇 | 32973-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 2-(1-苯基-3,4-二氢-1H-异喹啉-2-基)-乙醇
• 中文别名: 2-(1-苯基-3,4-二氢异喹啉-2(1H)-基)乙醇
• 英文名称: N-(2-hydroxyethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(2-hydroxyethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline；1-Phenyl-2-(β-oxyethyl)-tetrahydro-isochinolin；2-(1-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanol；2-(1-Phenyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanol；2-(1-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanol
• CAS: 32973-53-8
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: AFOUAOIZHNGJNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-(1-苯基-3,4-二氢-1H-异喹啉-2-基)-乙醇 在 PPA 、 氨 、 sodium 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 26.0h， 生成 7-Methyl-5,6,7,8,9,14-hexahydrodibenzo[d,g]azecine
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j
• 作为产物：
  描述：

  1-苯基-3,4-二氢异喹啉 在 platinum(IV) oxide 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 90.0 ℃ 、400.0 kPa 条件下， 反应 56.0h， 生成 2-(1-苯基-3,4-二氢-1H-异喹啉-2-基)-乙醇
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j

文献信息

• Vlaeminck, F.; Cock, E. De; Tourwe, D., Heterocycles, 1981, vol. 15, # 2, p. 1213 - 1218
  作者：Vlaeminck, F.、Cock, E. De、Tourwe, D.、Binst, G. Van

  DOI：——

  日期：——
• VLAEMINCK F.; COCK E. DE; TOURWE D.; BINST G. VAN, HETEROCYCLES, 1981, 15, NO 2, SPEC. ISSUE, 1213-1218
  作者：VLAEMINCK F.、 COCK E. DE、 TOURWE D.、 BINST G. VAN

  DOI：——

  日期：——
• Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist
  作者：Barbara Hoefgen、Michael Decker、Patrick Mohr、Astrid M. Schramm、Sherif A. F. Rostom、Hussein El-Subbagh、Peter M. Schweikert、Dirk R. Rudolf、Matthias U. Kassack、Jochen Lehmann

  DOI：10.1021/jm050846j

  日期：2006.1.1

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.