1-(1,3-Dihydro-isoindol-2-yl)-2-{4-[2-(2-hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-ethanone | 139734-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-(1,3-Dihydro-isoindol-2-yl)-2-{4-[2-(2-hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-ethanone
• 英文别名: 1-(1,3-Dihydroisoindol-2-yl)-2-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]ethanone
• CAS: 139734-29-5
• 化学式: C₂₇H₃₀N₂O₅
• 分子量: 462.546
• InChiKey: ZMNOEULDIBOSPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-chloro-1-(1,3-dihydro-2H-isoindol-2-yl)ethanone 、 p-(2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy)phenol 在 sodium hydride 作用下， 生成 1-(1,3-Dihydro-isoindol-2-yl)-2-{4-[2-(2-hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-ethanone
  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

• 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.