N-benzyl-N-<2-(4-hydroxyphenoxy)ethyl>-2-hydroxy-3-phenoxypropylamine | 107332-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-benzyl-N-<2-(4-hydroxyphenoxy)ethyl>-2-hydroxy-3-phenoxypropylamine
• 英文别名: N-benzyl-N-(2-p-hydroxyphenoxyethyl)-2-hydroxy-3-phenoxypropylamine；4-[2-[benzyl-(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenol
• CAS: 107332-60-5
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: SYNLIGYCDMFOQE-UHFFFAOYSA-N

物化性质

• 沸点：
  588.4±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-<2-(4-hydroxyphenoxy)ethyl>-2-hydroxy-3-phenoxypropylamine 在 palladium on activated charcoal 甲酸 、 氢气 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 60.0~100.0 ℃ 、2.0 MPa 条件下， 反应 75.0h， 生成 methyl N-methyl-<4-<2-<(2-hydroxy-3-phenoxypropyl)amino>ethoxy>phenoxy>acetate
  参考文献：
  名称：

  Selective .beta.3-adrenergic agonists of brown adipose tissue and thermogenesis. 2. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetamides

  摘要：

  The ester methyl [4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate (1) (R1 = OMe) had previously been identified as the most interesting member of a series of selective beta-3-adrenergic agonists of brown adipose tissue and thermogenesis in the rat. In vivo it acts mainly via the related acid 1 (R1 = OH). Amides have been examined to determine whether they have advantages over the ester. In particular, in the rat and dog the half-lives of amides of appropriate potency were no longer than those of the ester. The amide (S)-4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]-N-(2-methoxyethyl)phenoxyacetamide [S-27, ICI D7114] was selected as having properties consistent with a sustained-release formulation should that prove necessary. Unlike the ester it is resistant to hydrolysis in the gut lumen. Further testing of ICI D7114 has shown that in the rat, cat, and dog it stimulates the beta-3-adrenergic receptor in brown adipose tissue at doses lower than those at which it affects beta-1- and beta-2-adrenergic receptors in other tissues. Slimming effects were observed in the dog. ICI D7114 may be a selective thermogenic agent in man and may be useful in the treatment of obesity and diabetes.

  DOI：

  10.1021/jm00088a010
• 作为产物：
  描述：

  苯基缩水甘油醚 、 4-[2-(N-benzylamino)ethoxy]phenol 以 异丙醇 为溶剂， 反应 72.0h， 以to give N-benzyl-N-(2-p-hydroxyphenoxyethyl)-2-hydroxy-3-phenoxypropylamine as an oil which的产率得到N-benzyl-N-<2-(4-hydroxyphenoxy)ethyl>-2-hydroxy-3-phenoxypropylamine
  参考文献：
  名称：

  Phenyl ethers

  摘要：

  该发明涉及一系列新型苯氧乙酸醚（及其药学上可接受的盐），其化学式为I，其中R.sup.1为H或F，R.sup.2和R.sup.3为H或（1-3C）烷基，Z为CH.sub.2OH或一个基团--CO.R.sup.4，在其中R.sup.4为OH，NH.sub.2或（1-6C）烷氧基。该发明还包括用于治疗肥胖症及相关疾病的制药组合物，并提供制备新型醚的过程。

  公开号：

  US04772631A1

文献信息

• Amide derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04927836A1

  公开（公告）日：1990-05-22

  The invention concerns novel phenoxyacetic acid amide derivatives of the formula I (and pharmaceutically acceptable salts thereof) in which R.sup.1 is hydrogen or fluoro, R.sup.2 is phenyl, cycloalkyl, alkyl or alkenyl as defined herein, and R.sup.3 is hydrogen, methyl or ethyl, or R.sup.2 and R.sup.3 together form polymethylene as defined herein. The invention also includes pharmaceutical compositions containing the amide derivatives, means for the manufacture of the said derivatives and for their use in the treatment of obesity and related conditions and/or in the manufacture of novel medicaments.

  该发明涉及公式I的新颖苯氧乙酸酰胺衍生物（及其药用可接受的盐），其中R.sup.1为氢或氟，R.sup.2为苯基，环烷基，烷基或烯基，如本文所定义，R.sup.3为氢，甲基或乙基，或R.sup.2和R.sup.3共同形成聚亚甲基，如本文所定义。该发明还包括含有酰胺衍生物的药物组合物，用于制造所述衍生物的手段，以及用于治疗肥胖和相关疾病和/或制造新型药物的用途。
• 2-Hydroxy-3-phenoxypropyl amines
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0210849B1

  公开（公告）日：1990-08-29
• US4772631A
  申请人：——

  公开号：US4772631A

  公开（公告）日：1988-09-20
• US4927836A
  申请人：——

  公开号：US4927836A

  公开（公告）日：1990-05-22
• US4977148A
  申请人：——

  公开号：US4977148A

  公开（公告）日：1990-12-11