5-bromoindoline-1-thiocarboxamide | 201470-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-bromoindoline-1-thiocarboxamide
• 英文别名: 5-bromo-2,3-dihydroindole-1-carbothioamide
• CAS: 201470-79-3
• 化学式: C₉H₉BrN₂S
• 分子量: 257.154
• InChiKey: LSEIOKXUPCRWGE-UHFFFAOYSA-N

物化性质

• 沸点：
  376.1±52.0 °C(Predicted)
• 密度：
  1.691±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromoindoline-1-thiocarboxamide 在 N-氯代丁二酰亚胺 、 正丁基锂 、 二氧化硫 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Potent, selective human β3 adrenergic receptor agonists containing a substituted indoline-5-sulfonamide pharmacophore

  摘要：

  A series of compounds possessing an N-substituted indoline-5-sulfonamide pharmacophore was prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. The SAR of a wide range of urea and heterocyclic substituents is discussed. 4-Octyl thiazole compound 8c was the most potent and selective compound in the series, with 2800-fold selectivity over beta(1) binding and 1400-fold selectivity over beta(2) binding (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00277-2
• 作为产物：
  描述：

  5-溴二氢吲哚 以 盐酸 为溶剂， 生成 5-bromoindoline-1-thiocarboxamide
  参考文献：
  名称：

  Substituted sulfonamides as selective .beta.-3 agonists for the

  摘要：

  取代磺酰胺类化合物是选择性β3肾上腺素能受体激动剂，其β1和β2肾上腺素能受体活性极少，因此这些化合物能够增加细胞内脂肪分解和能量消耗，因此在治疗II型糖尿病和肥胖症方面具有强效活性。这些化合物还可用于降低甘油三酯水平和胆固醇水平或提高高密度脂蛋白水平或减少肠道运动。此外，这些化合物可用于减少神经源性炎症或作为抗抑郁剂。这些化合物是通过将氨基烷基苯磺酰胺与适当取代的环氧化合物偶联制备而成。本文还公开了使用这些化合物治疗糖尿病和肥胖症以及降低甘油三酯水平和胆固醇水平或提高高密度脂蛋白水平或增加肠道运动的组合物和方法。

  公开号：

  US05705515A1

文献信息

• US5705515A
  申请人：——

  公开号：US5705515A

  公开（公告）日：1998-01-06
• Potent, selective human β3 adrenergic receptor agonists containing a substituted indoline-5-sulfonamide pharmacophore
  作者：Robert J Mathvink、Anna Maria Barritta、Mari R Candelore、Margaret A Cascieri、Liping Deng、Laurie Tota、Catherine D Strader、Matthew J Wyvratt、Michael H Fisher、Ann E Weber

  DOI：10.1016/s0960-894x(99)00277-2

  日期：1999.7

  A series of compounds possessing an N-substituted indoline-5-sulfonamide pharmacophore was prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. The SAR of a wide range of urea and heterocyclic substituents is discussed. 4-Octyl thiazole compound 8c was the most potent and selective compound in the series, with 2800-fold selectivity over beta(1) binding and 1400-fold selectivity over beta(2) binding (C) 1999 Elsevier Science Ltd. All rights reserved.
• Substituted sulfonamides as selective .beta.-3 agonists for the
  申请人：Merck & Co., Inc.

  公开号：US05705515A1

  公开（公告）日：1998-01-06

  Substituted sulfonamides are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.

  取代磺酰胺类化合物是选择性β3肾上腺素能受体激动剂，其β1和β2肾上腺素能受体活性极少，因此这些化合物能够增加细胞内脂肪分解和能量消耗，因此在治疗II型糖尿病和肥胖症方面具有强效活性。这些化合物还可用于降低甘油三酯水平和胆固醇水平或提高高密度脂蛋白水平或减少肠道运动。此外，这些化合物可用于减少神经源性炎症或作为抗抑郁剂。这些化合物是通过将氨基烷基苯磺酰胺与适当取代的环氧化合物偶联制备而成。本文还公开了使用这些化合物治疗糖尿病和肥胖症以及降低甘油三酯水平和胆固醇水平或提高高密度脂蛋白水平或增加肠道运动的组合物和方法。