N-<2-(4-methoxyphenyl)-2-hydroxyethyl>-2-(3,4-dimethoxy-2-fluorophenyl)acetamide | 104421-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-<2-(4-methoxyphenyl)-2-hydroxyethyl>-2-(3,4-dimethoxy-2-fluorophenyl)acetamide
• 英文别名: 2-(2-fluoro-3,4-dimethoxyphenyl)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]acetamide
• CAS: 104421-99-0
• 化学式: C₁₉H₂₂FNO₅
• 分子量: 363.386
• InChiKey: CTQFEPZQRWOACE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-<2-(4-methoxyphenyl)-2-hydroxyethyl>-2-(3,4-dimethoxy-2-fluorophenyl)acetamide 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以74%的产率得到N-<2-hydroxy-2-(4-methoxyphenyl)>-2-(3,4-dimethoxy-2-fluorophenyl)ethylamine
  参考文献：
  名称：

  Dopamine agonists related to 3-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol, 6-position modifications

  摘要：

  The N-allyl derivative (SK&F 85174) of 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol (SK&F 82526) retains the DA-1 agonist potency of the latter compound but unlike the parent also shows substantial DA-2 agonist activity. In a previous study of N-substituted benzazepines these combined agonist effects were shown to be uniquely associated with the N-allyl group. A continuation of this research has examined dependency of combined DA-2/DA-1 agonist activities on 6-position modification with the specific objective of developing an agonist with maximum effectiveness and potency at the DA-2 receptor subtype. DA-2 agonist activity was measured in a rabbit ear artery assay, and DA-1 agonist activity was determined in an adenylate cyclase assay. Replacing chloro with bromo retains the activity pattern and the potency of the chloro compound; replacement with a hydrogen causes a decrease of both DA-1 and DA-2 receptor activating potency. Introduction of a 6-methyl group causes loss of DA-2 agonist activity and reduction in DA-1 agonist potency. Substitution with a 6-fluoro provides the best balance of DA-2 and DA-1 agonist activities; this compound was moderately potent in both assays.

  DOI：

  10.1021/jm00384a006
• 作为产物：
  描述：

  2-羟基-2-(4-甲氧基苯基)乙腈 在 sodium hydroxide 、 硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-<2-(4-methoxyphenyl)-2-hydroxyethyl>-2-(3,4-dimethoxy-2-fluorophenyl)acetamide
  参考文献：
  名称：

  Dopamine agonists related to 3-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol, 6-position modifications

  摘要：

  The N-allyl derivative (SK&F 85174) of 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol (SK&F 82526) retains the DA-1 agonist potency of the latter compound but unlike the parent also shows substantial DA-2 agonist activity. In a previous study of N-substituted benzazepines these combined agonist effects were shown to be uniquely associated with the N-allyl group. A continuation of this research has examined dependency of combined DA-2/DA-1 agonist activities on 6-position modification with the specific objective of developing an agonist with maximum effectiveness and potency at the DA-2 receptor subtype. DA-2 agonist activity was measured in a rabbit ear artery assay, and DA-1 agonist activity was determined in an adenylate cyclase assay. Replacing chloro with bromo retains the activity pattern and the potency of the chloro compound; replacement with a hydrogen causes a decrease of both DA-1 and DA-2 receptor activating potency. Introduction of a 6-methyl group causes loss of DA-2 agonist activity and reduction in DA-1 agonist potency. Substitution with a 6-fluoro provides the best balance of DA-2 and DA-1 agonist activities; this compound was moderately potent in both assays.

  DOI：

  10.1021/jm00384a006

文献信息

• ROSS S. T.; FRANZ R. G.; GALLAGHER G.; BRENNER M.; WILSON J. W.; DEMARINI+, J. MED. CHEM., 30,(1987) N 1, 35-40
  作者：ROSS S. T.、 FRANZ R. G.、 GALLAGHER G.、 BRENNER M.、 WILSON J. W.、 DEMARINI+

  DOI：——

  日期：——