2-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide | 42834-42-4

• 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-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide
• 英文别名: 2-(beta-[2-dimethylaminoethyl]-beta-hydroxyphenethyl)-N-methylbenzamide；2-[4-(dimethylamino)-2-hydroxy-2-phenylbutyl]-N-methylbenzamide
• CAS: 42834-42-4
• 化学式: C₂₀H₂₆N₂O₂
• 分子量: 326.439
• InChiKey: ALHCAEQCMKWFPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide 在 氮气 、 邻二氯苯 、 乙醚 作用下， 以 邻二氯苯 为溶剂， 反应 18.0h， 以to give 3-[2-dimethylaminoethyl]-3,4-dihydro-3-phenylisocoumarin的产率得到3,4-dihydro-3-<2-(N,N-dimethylamino)ethyl>-3-phenyl-1H-2-benzopyran-1-one
  参考文献：
  名称：

  10-(2-Substituted-amino-

  摘要：

  这段英文的翻译如下： 10-(2-取代氨基乙基)-10,11-二氢-5-亚甲基-2或3-7或8-取代或未取代-5H-二苯并[a,d]环庚烯，例如，10-(2-二甲基氨基乙基)-10,11-二氢-5-亚甲基-5H-二苯并[a,d]环庚烷，通过各种方法制备，包括对应的二苯并[a,d]环庚烯-5-醇的酸脱水。这些化合物可用作抗抑郁剂。

  公开号：

  US03994961A1
• 作为产物：
  描述：

  N-甲基邻甲苯酰胺 、 β-(二甲氨基)苯丙酮 盐酸盐 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide
  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

• 10-(2-Substituted-amino-
  申请人：Sandoz, Inc.

  公开号：US03994961A1

  公开（公告）日：1976-11-30

  10-(2-substituted-aminoethyl)-10,11-dihydro-5-methylene-2 or 3 7 or 8-substituted or unsubstituted-5H-dibenzo[a,d]cycloheptenes e.g., 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cyclohe ptane, prepared by various methods including acid dehydration of the corresponding dibenzo[a,d]cycloheptene-5-ols. The compounds are useful as anti-depressants.

  10-(2-取代氨基乙基)-10,11-二氢-5-甲基-2或3-7或8-取代或未取代-5H-二苯并[a,d]环庚烯，例如10-(2-二甲基氨基乙基)-10,11-二氢-5-甲基-5H-二苯并[a,d]环庚烷，通过包括对应的二苯并[a,d]环庚烯-5-醇的酸脱水等各种方法制备。这些化合物可用作抗抑郁药。
• 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.
• 10-(2-Substituted-amino-ethyl)-10,11-dihydro-5-meth
  申请人：Sandoz, Inc.

  公开号：US04083997A1

  公开（公告）日：1978-04-11

  10-(2-substituted-aminoethyl)-10,11-dihydro-5-methylene-2 or 3 7 or 8-substituted or unsubstituted-5H-dibenzo[a,d]cycloheptenes e.g., 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cyclohe ptene, prepared by various methods including acid dehydration of the corresponding dibenzo[a,d]cycloheptene-5-ols. The compounds are useful as anti-depressants.

  用各种方法制备的10-(2-取代氨基乙基)-10,11-二氢-5-亚甲基-2或3、7或8-取代或未取代-5H-二苯并[a,d]环庚烯，例如10-(2-二甲基氨基乙基)-10,11-二氢-5-亚甲基-5H-二苯并[a,d]环庚烯，通过相应的二苯并[a,d]环庚烯-5-醇的酸脱水制备。这些化合物可用作抗抑郁剂。