(2E,4E)-5-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)penta-2,4-dienoic acid | 118420-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4E)-5-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)penta-2,4-dienoic acid
• CAS: 118420-17-0
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: MNQUCSBHAUUDQX-YDFGWWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.65
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)penta-2,4-dienoic acid 在 盐酸 作用下， 生成 (2E,4E)-5-(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-yl)-penta-2,4-dienoic acid [4-(4-benzhydryl-piperazin-1-yl)-butyl]-amide
  参考文献：
  名称：

  Acrylamide derivatives as antiallergic agents. 2. Synthesis and structure activity relationships of N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(3-pyridyl)acrylamides

  摘要：

  A new series of 3-(3-pyridyl)acrylamides 16, 17, 19, and 26, and 5-(3-pyridyl)-2,4-pentadienamides 20-25 were prepared and evaluated for their antiallergic activity. Several of these compounds exhibited more potent inhibitory activities than the parent compound 1a [(E)-N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3- (3-pyridyl)acrylamide] against the rat passive cutaneous anaphylaxis (PCA) reaction and the enzyme 5-lipoxygenase. Particularly, (E)-N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3- (6-methyl-3-pyridyl)acrylamide (17p) showed an ED50 value of 3.3 mg/kg po in the rat PCA test, which was one-fifth of ketotifen and oxatomide. As compared with ketotifen and oxatomide, compound 17p (AL-3264) possessed a better balance of antiallergic properties due to inhibition of chemical mediator release, inhibition of 5-lipoxygenase, and antagonism of histamine.

  DOI：

  10.1021/jm00123a012
• 作为产物：
  描述：

  alpha4,3-异亚丙基异吡哆醛 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 生成 (2E,4E)-5-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)penta-2,4-dienoic acid
  参考文献：
  名称：

  Acrylamide derivatives as antiallergic agents. 2. Synthesis and structure activity relationships of N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(3-pyridyl)acrylamides

  摘要：

  A new series of 3-(3-pyridyl)acrylamides 16, 17, 19, and 26, and 5-(3-pyridyl)-2,4-pentadienamides 20-25 were prepared and evaluated for their antiallergic activity. Several of these compounds exhibited more potent inhibitory activities than the parent compound 1a [(E)-N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3- (3-pyridyl)acrylamide] against the rat passive cutaneous anaphylaxis (PCA) reaction and the enzyme 5-lipoxygenase. Particularly, (E)-N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3- (6-methyl-3-pyridyl)acrylamide (17p) showed an ED50 value of 3.3 mg/kg po in the rat PCA test, which was one-fifth of ketotifen and oxatomide. As compared with ketotifen and oxatomide, compound 17p (AL-3264) possessed a better balance of antiallergic properties due to inhibition of chemical mediator release, inhibition of 5-lipoxygenase, and antagonism of histamine.

  DOI：

  10.1021/jm00123a012