(2-{2-[4-(4-Carbamoyl-butyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester | 374108-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2-{2-[4-(4-Carbamoyl-butyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester
• CAS: 374108-83-5
• 化学式: C₂₄H₂₈N₂O₆
• 分子量: 440.496
• InChiKey: PPJSPUHJQYMUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108.16
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2-{2-[4-(4-Carbamoyl-butyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (2-{2-[4-(4-Carbamoyl-butyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid
  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
• 作为产物：
  描述：

  5-{2-[2-(2-Methoxycarbonylmethyl-phenoxy)-ethyl]-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl}-pentanoic acid 在 N,N'-羰基二咪唑 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2-{2-[4-(4-Carbamoyl-butyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester
  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