methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate | 942999-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate
• 英文别名: methyl 2-[4-[4-(2-bromo-2-methylpropanoyl)phenyl]-1-bicyclo[2.2.2]octanyl]acetate
• CAS: 942999-70-4
• 化学式: C₂₁H₂₇BrO₃
• 分子量: 407.348
• InChiKey: OMBBMVIAVBYWKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate 、 4,5-二氨基-6-羟基嘧啶 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以64%的产率得到methyl {4-[4-(4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]-oxazin-6-yl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate
  参考文献：
  名称：

  Discovery of a Potent, Selective, and Orally Efficacious Pyrimidinooxazinyl Bicyclooctaneacetic Acid Diacylglycerol Acyltransferase-1 Inhibitor

  摘要：

  Inhibition of DGAT-1 is increasingly seen as an attractive mechanism with the potential for treatment of obesity and other elements of the metabolic syndrome. We report here a bicyclooctaneacetic acid derivative in the pyrimidinooxazine structural class of DGAT-1 inhibitors that has good potency, selectivity, and pharmacokinetic characteristics across a variety of species. This compound is an effective inhibitor of DGAT-1 in both intestinal and adipose tissue, which results in a reduction in body weight or body weight gain following oral administration in both mouse and rat models of dietary-induced obesity.

  DOI：

  10.1021/jm801507v
• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 methyl 2-(4-phenylbicyclo[2.2.2]octan-1-yl)acetate 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate
  参考文献：
  名称：

  Discovery of a Potent, Selective, and Orally Efficacious Pyrimidinooxazinyl Bicyclooctaneacetic Acid Diacylglycerol Acyltransferase-1 Inhibitor

  摘要：

  Inhibition of DGAT-1 is increasingly seen as an attractive mechanism with the potential for treatment of obesity and other elements of the metabolic syndrome. We report here a bicyclooctaneacetic acid derivative in the pyrimidinooxazine structural class of DGAT-1 inhibitors that has good potency, selectivity, and pharmacokinetic characteristics across a variety of species. This compound is an effective inhibitor of DGAT-1 in both intestinal and adipose tissue, which results in a reduction in body weight or body weight gain following oral administration in both mouse and rat models of dietary-induced obesity.

  DOI：

  10.1021/jm801507v

文献信息

• Pyrimido [4,5-B] -Oxazines For Use as Dgat Inhibitors
  申请人：Birch Alan Martin

  公开号：US20080306059A1

  公开（公告）日：2008-12-11

  Compounds of formula (I) or salts thereof, wherein A, and R 1 to R 5 are as defined in the specification, are DGAT-1 inhibitors and are thereby useful in the treatment of, for example, obesity. Processes to make compounds of formula (I) are also described.

  化合物公式（I）或其盐，其中A和R1至R5如规范中所定义，是DGAT-1抑制剂，因此在治疗肥胖等方面非常有用。本文还描述了制备化合物公式（I）的过程。
• Pyrimido [4,5-B] -Oxazines for use as DGAT inhibitors
  申请人：AstraZeneca AB

  公开号：US07749997B2

  公开（公告）日：2010-07-06

  Compounds of formula (I) or salts thereof, wherein A, and R1 to R5 are as defined in the specification, are DGAT-1 inhibitors and are thereby useful in the treatment of, for example, obesity. Processes to make compounds of formula (I) are also described.

  式(I)的化合物或其盐，其中A和R1至R5如规范所定义，是DGAT-1抑制剂，因此在治疗肥胖症等方面有用。还描述了制备式(I)化合物的过程。
• Pyrimido [4,5-B]-oxazines for use as DGAT inhibitors
  申请人：AstraZeneca AB

  公开号：US08017603B2

  公开（公告）日：2011-09-13

  Compounds of formula (I) or salts thereof, wherein A, and R1 to R5 are as defined in the specification, are DGAT-1 inhibitors and are thereby useful in the treatment of, for example, obesity. Processes to make compounds of formula (I) are also described.

  公式（I）的化合物或其盐，其中A和R1至R5如规范所定义，是DGAT-1抑制剂，因此在治疗肥胖等方面是有用的。本文还描述了制备公式（I）化合物的过程。
• PYRIMIDO [4,5-B] -OXAZINES FOR USE AS DGAT INHIBITORS
  申请人：Birch Alan Martin

  公开号：US20100311737A1

  公开（公告）日：2010-12-09

  Compounds of formula (I) or salts thereof, wherein A, and R 1 to R 5 are as defined in the specification, are DGAT-1 inhibitors and are thereby useful in the treatment of, for example, obesity. Processes to make compounds of formula (I) are also described.

  式(I)化合物或其盐，其中A和R1到R5如规范中所定义，是DGAT-1抑制剂，因此在治疗肥胖症等方面有用。本文还描述了制备式(I)化合物的过程。
• WO2007/71966
  申请人：——

  公开号：——

  公开（公告）日：——