4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide | 115656-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide
• 英文别名: 2-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]-N-(2-methoxyethyl)acetamide
• CAS: 115656-32-1
• 化学式: C₂₂H₃₀N₂O₆
• 分子量: 418.49
• InChiKey: RVMBDLSFFNKKLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  98.3
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl <4-<2-<(2-hydroxy-3-phenoxypropyl)amino>ethoxy>phenoxy>acetate 、 2-甲氧基乙胺 以 甲苯 为溶剂， 生成 4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide
  参考文献：
  名称：

  Selective .beta.3-adrenergic agonists of brown adipose tissue and thermogenesis. 1. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetates

  摘要：

  The ester methyl [4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate (8) has 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 10. Potency was generally markedly reduced by placing substituents on the phenyl ring of the phenoxypropanolamine unit of 8; only the 2-fluoro analogue 16 had comparable potency to 8. Other structure-activity relationships are discussed. Further testing of 8 (ICI 198157) has shown that in the rat 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. It increases metabolic rate, as judged by an increase in oxygen consumption, and in the genetically obese Zucker rat it causes a reduced rate of weight gain. This class of compound may be useful in the treatment of obesity in man.

  DOI：

  10.1021/jm00088a009

文献信息

• Amide derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0254532B1

  公开（公告）日：1990-05-09
• US4927836A
  申请人：——

  公开号：US4927836A

  公开（公告）日：1990-05-22
• [EN] THERAPEUTIC AGENTS FOR THE TREATMENT OF CACHEXIA<br/>[FR] AGENTS THERAPEUTIQUES POUR LE TRAITEMENT DE LA CACHEXIE
  申请人：——

  公开号：WO1994012166A1

  公开（公告）日：1994-06-09

  [EN] The use of 4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]-N-(2-methoxyethyl)phenoxy acetamide or its acid metabolite in the treatment of cachexia and in particular cancer cachexia.
  [FR] L'invention concerne l'utilisation du 4-[2-[(2-hydroxy-3-phénoxypropyl)amino]éthoxy]-N-(2-méthoxyéthyl)phénoxy acétamide ou son métabolite d'acide correspondant, dans le traitement de la cachexie et en particulier de la cachexie liée au cancer.
• Selective .beta.3-adrenergic agonists of brown adipose tissue and thermogenesis. 1. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetates
  作者：Ralph Howe、Balbir S. Rao、Brian R. Holloway、Donald Stribling

  DOI：10.1021/jm00088a009

  日期：1992.5

  The ester methyl [4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate (8) has 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 10. Potency was generally markedly reduced by placing substituents on the phenyl ring of the phenoxypropanolamine unit of 8; only the 2-fluoro analogue 16 had comparable potency to 8. Other structure-activity relationships are discussed. Further testing of 8 (ICI 198157) has shown that in the rat 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. It increases metabolic rate, as judged by an increase in oxygen consumption, and in the genetically obese Zucker rat it causes a reduced rate of weight gain. This class of compound may be useful in the treatment of obesity in man.