6-hydroxy-7-tert-butyl-1,4-benzodioxin-2-carboxylic acid ethyl ester | 160657-96-5

• 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-hydroxy-7-tert-butyl-1,4-benzodioxin-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 7-tert-butyl-6-hydroxy-1,4-benzodioxine-2-carboxylate
• CAS: 160657-96-5
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: AIUUJQHJAGOSRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxy-7-tert-butyl-1,4-benzodioxin-2-carboxylic acid ethyl ester 在 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 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N-butyl-7-tert-butyl-6-hydroxy-N-phenyl-1,4-benzodioxine-2-carboxamide
  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-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 乙醇 、 sodium ethanolate 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 6-hydroxy-7-tert-butyl-1,4-benzodioxin-2-carboxylic acid ethyl ester
  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

文献信息

• US5420132A
  申请人：——

  公开号：US5420132A

  公开（公告）日：1995-05-30
• US5439909A
  申请人：——

  公开号：US5439909A

  公开（公告）日：1995-08-08
• 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
  作者：Valérie Thiéry、Gérard Coudert、Jean-Guy Bizot-Espiard、Bruno Pfeiffer、Pierre Renard、Albert Lindenbaum、Gérald Guillaumet

  DOI：10.1021/jm0108045

  日期：2001.11.1

  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.