Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(6-methanesulfonamidohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(6-methanesulfonamidohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-
• 英文别名: 2-[2-[2-[4-[6-(Methanesulfonamido)hexyl]-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]acetic acid
• 化学式: C₂₅H₃₂N₂O₇S
• 分子量: 504.604
• InChiKey: XXCUJNNYVKJWNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  硝苯酚 在 palladium on activated charcoal 咪唑 、 sodium hydroxide 、 三丁基膦 、 TEA 、 氢气 、 sodium hydride 、 potassium carbonate 、 肼 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 60.0 ℃ 、310.26 kPa 条件下， 反应 37.5h， 生成 Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(6-methanesulfonamidohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-
  参考文献：
  名称：

  Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

  摘要：

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm0301888

文献信息

• Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model
  作者：Philip J. Rybczynski、Roxanne E. Zeck、Joseph Dudash、Donald W. Combs、Thomas P. Burris、Maria Yang、Melville C. Osborne、Xiaoli Chen、Keith T. Demarest

  DOI：10.1021/jm0301888

  日期：2004.1.1

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.