2-(3-methoxyphenylethylamino)-1-phenylethanol | 63166-03-0

• 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: 2-(3-methoxyphenylethylamino)-1-phenylethanol
• 英文别名: N-[2-(3-methoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine；2-[2-(3-methoxyphenyl)ethylamino]-1-phenylethanol
• CAS: 63166-03-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: VBGNBQHXGIMWTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenylethylamino)-1-phenylethanol 在 硫酸 、 三氟乙酸 作用下， 反应 3.0h， 生成 7-Methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

  摘要：

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.

  DOI：

  10.1021/jm0700417
• 作为产物：
  描述：

  氧化苯乙烯 生成 2-(3-methoxyphenylethylamino)-1-phenylethanol
  参考文献：
  名称：

  BONDINELL, WILLIAM E.;WEN-FU, KU THOMAS;ORMSBEE, HERBERT S. (III)

  摘要：

  DOI：

文献信息

• Pharmaceutical compositions and methods involving benzazepine derivatives
  申请人：SmithKline Corporation

  公开号：US04011319A1

  公开（公告）日：1977-03-08

  Pharmaceutical compositions and a method of stimulating peripheral dopamine receptors by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal. Renal vasodilator and diuretic methods are also disclosed.

  药用组合物及通过向动物体内施用非毒性有效量的苯并氮杂卓衍生物来刺激外周多巴胺受体的方法。还公开了肾血管扩张剂和利尿剂的方法。
• 1-Phenyl-3-benzazepines
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0230755A1

  公开（公告）日：1987-08-05

  Compounds of the formula (1): and pharmaceutically acceptable acid addition salts are described wherein R1 is hydrogen, C1-C6 alkyl or C3-C5 alkenyl; R2 is hydrogen, hydroxy, C1-C6 alkoxy, halogen, trifluoromethyl, C,-C6 alkyl, SOnC1-C6 alkyl, SOnCF3, SOnphenyl or SO2NR6R7; R3 is hydrogen, C1-C6-alkyl or C1-C6 alkanoyl; R4 is SOnR5 or SO2NR6R7; n is 0, 1 or 2; R is or trifluoromethyl; and R6 and R7 are hydrogen or C1-C6 alkyl. These compounds are useful in the treatment of gastrointestinal motility disorders. Pharmaceutical compositions and methods of use are described. Intermediates and processes for the preparation of compounds of the formula (1) are described.

  式（1）的化合物： 及药学上可接受的酸加成盐，其中 R1 是氢、C1-C6 烷基或 C3-C5 烯基；R2 是氢、羟基、C1-C6 烷氧基、卤素、三氟甲基、C,-C6 烷基、SOnC1-C6 烷基、SOnCF3、SOnphenyl 或 SO2NR6R7；R3 是氢、C1-C6 烷基或 C1-C6 烷酰基；R4 是 SOnR5 或 SO2NR6R7；n 是 0、1 或 2；R 是 或三氟甲基；以及 R6 和 R7 是氢或 C1-C6 烷基。这些化合物可用于治疗胃肠道运动障碍。描述了药物组合物和使用方法。描述了制备式（1）化合物的中间体和工艺。
• BONDINELL, WILLIAM E.;WEN-FU, KU THOMAS;ORMSBEE, HERBERT S. (III)
  作者：BONDINELL, WILLIAM E.、WEN-FU, KU THOMAS、ORMSBEE, HERBERT S. (III)

  DOI：——

  日期：——
• US4011319A
  申请人：——

  公开号：US4011319A

  公开（公告）日：1977-03-08
• Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1
  作者：Edwin S. Tan、Motonori Miyakawa、James R. Bunzow、David K. Grandy、Thomas S. Scanlan

  DOI：10.1021/jm0700417

  日期：2007.6.1

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.