2-[4-Dimethylamino-2-(4-fluoro-phenyl)-2-hydroxy-butyl]-N-methyl-benzamide | 55831-60-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[4-Dimethylamino-2-(4-fluoro-phenyl)-2-hydroxy-butyl]-N-methyl-benzamide
• 英文别名: 2-[4-(dimethylamino)-2-(4-fluorophenyl)-2-hydroxybutyl]-N-methylbenzamide
• CAS: 55831-60-2
• 化学式: C₂₀H₂₅FN₂O₂
• 分子量: 344.429
• InChiKey: CTZBUFZVCGXSQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-Dimethylamino-2-(4-fluoro-phenyl)-2-hydroxy-butyl]-N-methyl-benzamide 以 various solvent(s) 为溶剂， 反应 48.0h， 以100 mg的产率得到
  参考文献：
  名称：

  Isochromanone-based urotensin-II receptor agonists

  摘要：

  A series of analogues of the selective non-peptide urotensin II (UII) receptor agonist 3-(4-chlorophenyl)-3-(2-dimethylaminoethyl)-isochroman- 1-one (AC-7954, 1) was synthesized and evaluated for UII agonist activity using a functional cell-based assay. The introduction of a methyl group in the 4-position resulted in a complete loss of activity, whereas substituents in the aromatic rings were beneficial. Sterically demanding amino groups were also detrimental to the activity. Several potent agonists were identified, six compounds being equally or more potent than 1. The most potent compound in the series was the 6,7-dimethyl analogue of 1 (16, pEC(50) 6.87). The racemate of 16 was resolved into the pure enantiomers using preparative straight phase HPLC. It was shown that the potency resides in the (+)-enantiomer (pEC(50) 7.11). The synthesized compounds seem to be selective for the UII receptor as no activities were observed at the closely related SSTR3 and 5 receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.056
• 作为产物：
  描述：

  N-甲基邻甲苯酰胺 、 2-(4-fluorobenzoyl)-1-N,N-dimethylaminoethane hydrochloride 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-[4-Dimethylamino-2-(4-fluoro-phenyl)-2-hydroxy-butyl]-N-methyl-benzamide
  参考文献：
  名称：

  Isochromanone-based urotensin-II receptor agonists

  摘要：

  A series of analogues of the selective non-peptide urotensin II (UII) receptor agonist 3-(4-chlorophenyl)-3-(2-dimethylaminoethyl)-isochroman- 1-one (AC-7954, 1) was synthesized and evaluated for UII agonist activity using a functional cell-based assay. The introduction of a methyl group in the 4-position resulted in a complete loss of activity, whereas substituents in the aromatic rings were beneficial. Sterically demanding amino groups were also detrimental to the activity. Several potent agonists were identified, six compounds being equally or more potent than 1. The most potent compound in the series was the 6,7-dimethyl analogue of 1 (16, pEC(50) 6.87). The racemate of 16 was resolved into the pure enantiomers using preparative straight phase HPLC. It was shown that the potency resides in the (+)-enantiomer (pEC(50) 7.11). The synthesized compounds seem to be selective for the UII receptor as no activities were observed at the closely related SSTR3 and 5 receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.056

文献信息

• US3994961A
  申请人：——

  公开号：US3994961A

  公开（公告）日：1976-11-30
• US4083997A
  申请人：——

  公开号：US4083997A

  公开（公告）日：1978-04-11
• Isochromanone-based urotensin-II receptor agonists
  作者：Fredrik Lehmann、Erika A. Currier、Roger Olsson、Uli Hacksell、Kristina Luthman

  DOI：10.1016/j.bmc.2005.01.056

  日期：2005.4

  A series of analogues of the selective non-peptide urotensin II (UII) receptor agonist 3-(4-chlorophenyl)-3-(2-dimethylaminoethyl)-isochroman- 1-one (AC-7954, 1) was synthesized and evaluated for UII agonist activity using a functional cell-based assay. The introduction of a methyl group in the 4-position resulted in a complete loss of activity, whereas substituents in the aromatic rings were beneficial. Sterically demanding amino groups were also detrimental to the activity. Several potent agonists were identified, six compounds being equally or more potent than 1. The most potent compound in the series was the 6,7-dimethyl analogue of 1 (16, pEC(50) 6.87). The racemate of 16 was resolved into the pure enantiomers using preparative straight phase HPLC. It was shown that the potency resides in the (+)-enantiomer (pEC(50) 7.11). The synthesized compounds seem to be selective for the UII receptor as no activities were observed at the closely related SSTR3 and 5 receptors. (c) 2005 Elsevier Ltd. All rights reserved.