6-acetoxy-1,4-benzodioxin-2-carboxylic acid ethyl ester | 160657-93-2

• 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-acetoxy-1,4-benzodioxin-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 6-acetoxy-1,4-benzodioxin-2-carboxylate；ethyl 6-acetyloxy-1,4-benzodioxine-2-carboxylate
• CAS: 160657-93-2
• 化学式: C₁₃H₁₂O₆
• 分子量: 264.235
• InChiKey: OOJRKDZRNCJRRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-acetoxy-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87%的产率得到6-hydroxy-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
• 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 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 6-acetoxy-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

• Substituted benzodioxins
  申请人：Adir et Compagnie

  公开号：US05420132A1

  公开（公告）日：1995-05-30

  A compound of formula (I): ##STR1## wherein: X represents O, S or H.sub.2, R and R' each represents hydrogen or together form a bond, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description. useful in the treatment or prevention of disorders involving oxidative processes.

  式(I)的化合物：##STR1## 其中：X代表O、S或H.sub.2，R和R'各代表氢或共同形成键，R.sub.1、R.sub.2、R.sub.3和R.sub.4如描述中所定义。用于治疗或预防涉及氧化过程的疾病。
• New substituted benzodioxins
  申请人：Adir et Compagnie

  公开号：US05439909A1

  公开（公告）日：1995-08-08

  A compound of formula (I): ##STR1## wherein: X represents O, S or H.sub.2, R and R' each represents hydrogen or together form a bond, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description. useful in the treatment or prevention of disorders involving oxidative processes.

  式(I)的化合物：##STR1## 其中：X代表O，S或H.sub.2，R和R'分别代表氢或共同形成键，R.sub.1，R.sub.2，R.sub.3和R.sub.4如描述中所定义。在治疗或预防涉及氧化过程的疾病中有用。
• Anthracene compounds useful in treating certain cancers
  申请人：Adir et Compagnie

  公开号：US05807882A1

  公开（公告）日：1998-09-15

  A compound of formula (I): ##STR1## in which R.sup.1, R.sup.2, X and Y are as defined in the description, the isomers thereof and the addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same are useful in the treatment of certain cancers.

  式(I)的化合物：##STR1## 其中R.sup.1，R.sup.2，X和Y如描述中所定义，其异构体及其与药学上可接受的酸或碱的加合盐，以及含有其的药物制剂在治疗某些癌症方面是有用的。
• New and promising type of leukotriene B4 (LTB4) antagonists based on the 1,4-benzodioxine structure
  作者：Latifa Bouissane、Mostafa Khouili、Gérard Coudert、M. Dolors Pujol、Gérald Guillaumet

  DOI：10.1016/j.ejmech.2023.115332

  日期：2023.6

  allow the development of new types of structures based on 1,4-benzodioxine. Forty-one new 1,4-benzodioxine molecules substituted at different positions of the heterocyclic nucleus were synthesized to determine the minimum structural requirements by studying structure-activity relationships. Eighteen of them were tested in vitro and in vivo for their anti-inflammatory activity related to the antagonist

  新的白三烯 B4 (LTB4) 拮抗剂已被合成，可被视为潜在的抗炎药物。含有 1,4-苯并二恶英双氧化核的结构构成了一组潜在的白三烯 B4 (LTB4) 拮抗剂。本研究的目的是获得有效和选择性的 LTB4 拮抗剂，作为阐明 LTB4 在炎症过程中的作用的一种方式，从而允许开发基于 1,4-苯并二恶英的新型结构。合成了 41 个在杂环核不同位置取代的新 1,4-苯并二恶英分子，通过研究构效关系确定最低结构要求。其中十八个在体外和体内进行了测试因为它们的抗炎活性与 LTB4 的拮抗剂特性有关。药理学试验表明化合物24b、24c和24e具有令人满意的体外活性，IC50 分别为 288、439、477 nM。使用在体外试验24b中表现出更大活性的化合物进行的体内试验的结果显示出显着的抗炎特性。
• US5420132A
  申请人：——

  公开号：US5420132A

  公开（公告）日：1995-05-30