N-chloroacetyl-2,3,4,5-tetrahydroisoxazole | 139734-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-chloroacetyl-2,3,4,5-tetrahydroisoxazole
• 英文别名: N-chloroacetyl isooxazolidine；Ethanone, 2-chloro-1-(2-isoxazolidinyl)-；2-chloro-1-(1,2-oxazolidin-2-yl)ethanone
• CAS: 139734-56-8
• 化学式: C₅H₈ClNO₂
• 分子量: 149.577
• InChiKey: DFDVNGSQYAPYEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-2,3,4,5-tetrahydroisoxazole 、 p-(2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy)phenol 在 sodium hydride 作用下， 生成 2-{4-[2-(2-Hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-1-isoxazolidin-2-yl-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
• 作为产物：
  描述：

  盐酸异恶唑烷 、 三乙胺 、 氯乙酰氯 在 三乙胺盐酸盐 、 乙醚 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以to give N-chloroacetyl isooxazolidine as an oil (11.5 g) NMR (CDCl3) 2.38[quintet, 2H, CH2 ], 3.78[t,2H, NCH2 ], 4.05[t,2H, OCH2 ]and 4.22 [s,2H, ClCH2CO]的产率得到N-chloroacetyl-2,3,4,5-tetrahydroisoxazole
  参考文献：
  名称：

  Chemical compounds

  摘要：

  本发明揭示了2-(2-羟基-3-苯氧基丙基氨基)乙基苯氧基乙酰胺化合物在肥胖症及相关疾病的治疗中的应用。本发明还描述了制备这些化合物的方法，以及包含它们的新型中间体和制药组合物。

  公开号：

  US04999377A1

文献信息

• 2-(2-Hydroxy-3-phenoxypropylamino)ethylphenoxyacetamides and processes and intermediates for their preparation
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0328251A2

  公开（公告）日：1989-08-16

  2-(2-Hydroxy-3-phenoxypropylamino)ethylphenoxyacetamide compounds are disclosed as useful in the treatment of obesity and related conditions. Processes for their preparation are described, as are novel intermediates and pharmaceutical compositions containing them.

  2-(2-羟基-3-苯氧基丙基氨基)乙基苯氧基乙酰胺化合物被公开用于治疗肥胖症和相关疾病。介绍了制备这些化合物的工艺，以及含有这些化合物的新型中间体和药物组合物。
• US4999377A
  申请人：——

  公开号：US4999377A

  公开（公告）日：1991-03-12
• 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.
• Chemical compounds
  申请人：Imperial Chemical Industries PLC

  公开号：US04999377A1

  公开（公告）日：1991-03-12

  2-(2-Hydroxy-3-phenoxypropylamino)ethylphenoxyacetamide compounds are disclosed as useful in the treatment of obesity and related conditions. Processes for their preparation are described, as are novel intermediates and pharmaceutical compositions containing them.

  2-(2-羟基-3-苯氧基丙基氨基)乙基苯氧乙酰胺化合物被披露为治疗肥胖和相关疾病的有效药物。描述了它们的制备方法，以及包含它们的新型中间体和药物组合物。