6-[N-(tert-butoxycarbonyl)amino]-1,4-benzodioxin-2-carboxylic acid | 380239-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 英文名称: 6-[N-(tert-butoxycarbonyl)amino]-1,4-benzodioxin-2-carboxylic acid
• 英文别名: 6-[(2-Methylpropan-2-yl)oxycarbonylamino]-1,4-benzodioxine-2-carboxylic acid
• CAS: 380239-21-4
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: UKGMSFJLDHZOPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[N-(tert-butoxycarbonyl)amino]-1,4-benzodioxin-2-carboxylic acid 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (6-Amino-benzo[1,4]dioxin-2-yl)-{4-[bis-(4-fluoro-phenyl)-methyl]-piperazin-1-yl}-methanone
  参考文献：
  名称：

  A Novel Series of 2,6,7-Substituted 2,3-Dihydro-1,4-Benzodioxin and 2,6,7-Substituted 1,4-Benzodioxin Derivatives as Lipid Peroxidation Inhibitors. Structure−Activity Relationships for High Inhibition of Human Low-Density Lipoprotein Peroxidation

  摘要：

  A series of 6- or 7-substituted 2-carboxamido- or 2-(aminomethyl)-1,4-benzodioxin and -2,3-dihydro-1,4-benzodioxin derivatives were synthesized and evaluated to determine the necessary structural requirements for a high inhibition of human low-density lipoprotein copper-induced peroxidation. The most active compounds (21, 25, 28, 36, and 37) were found between 5 and > 45 times more active than probucol itself. Due to both their potency and their structural features, compounds 25 and 36 were selected with others for complementary in vitro and in vivo investigations. Both of them exhibit calcium antagonist properties in the same range of potency as flunarizine itself. Compound 36 was also found to have significant hypolipaemic activity in mice at 100 and 300 mg/kg po, while compound 25 proved to be clearly active in a normobar hypoxia test.

  DOI：

  10.1021/jm0108045
• 作为产物：
  描述：

  6-N-tert-butoxycarbonylamino-1,4-benzodioxin-2-carboxylic acid ethyl ester 在 10percent aq. NaOH 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以95%的产率得到6-[N-(tert-butoxycarbonyl)amino]-1,4-benzodioxin-2-carboxylic acid
  参考文献：
  名称：

  A Novel Series of 2,6,7-Substituted 2,3-Dihydro-1,4-Benzodioxin and 2,6,7-Substituted 1,4-Benzodioxin Derivatives as Lipid Peroxidation Inhibitors. Structure−Activity Relationships for High Inhibition of Human Low-Density Lipoprotein Peroxidation

  摘要：

  A series of 6- or 7-substituted 2-carboxamido- or 2-(aminomethyl)-1,4-benzodioxin and -2,3-dihydro-1,4-benzodioxin derivatives were synthesized and evaluated to determine the necessary structural requirements for a high inhibition of human low-density lipoprotein copper-induced peroxidation. The most active compounds (21, 25, 28, 36, and 37) were found between 5 and > 45 times more active than probucol itself. Due to both their potency and their structural features, compounds 25 and 36 were selected with others for complementary in vitro and in vivo investigations. Both of them exhibit calcium antagonist properties in the same range of potency as flunarizine itself. Compound 36 was also found to have significant hypolipaemic activity in mice at 100 and 300 mg/kg po, while compound 25 proved to be clearly active in a normobar hypoxia test.

  DOI：

  10.1021/jm0108045