5-allyl-2,2-dimethyl-4-(3-pyridyl)-1,3-dioxane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-allyl-2,2-dimethyl-4-(3-pyridyl)-1,3-dioxane
• 英文别名: 5-allyl-2,2-dimethyl-4-(pyridin-3-yl)-1,3-dioxane；3-(2,2-Dimethyl-5-prop-2-enyl-1,3-dioxan-4-yl)pyridine
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: QTTLDKCCFAGVIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-allyl-2,2-dimethyl-4-(3-pyridyl)-1,3-dioxane 在 臭氧 作用下， 生成 (4S,5R)-<2,2-dimethyl-4-(3-pyridyl)-1,3-dioxan-5-yl>acetaldehyde 、 trans-<2,2-dimethyl-4-(3-pyridyl)-1,3-dioxan-5yl>acetaldehyde
  参考文献：
  名称：

  Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors: Synthesis and Biological Properties of [2-Substituted-4-(3-pyridyl)-1,3-dioxan-5-yl]alkenoic Acids

  摘要：

  The design, synthesis, and pharmacology of a new class of compounds possessing both thromboxane receptor antagonist and thromboxane synthase inhibitory properties are described. Replacement of the phenol group of the known thromboxane antagonist series 4(Z)-6-[(4RS,5SR)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid by a 3-pyridyl group led to a series of compounds, 5, which were potent thromboxane synthase inhibitors and weak thromboxane antagonists. Further modifications at the dioxane C2 position led to compounds, 7, which were potent dual-acting agents. In the case of compound 7w, the dual activity was shown to reside almost exclusively in the (-)-enantiomer, 7x. Following oral dosing to rats and dogs, 7x (3 mg/kg) displayed significant dual activity over a period of at least 8 h.

  DOI：

  10.1021/jm00004a014
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 methyl (2S)-2-<(1S)-1-hydroxy-1-(3-pyridyl)methyl>pent-4-enoate 在 对甲苯磺酸 作用下， 以 乙酸乙酯 为溶剂， 生成 5-allyl-2,2-dimethyl-4-(3-pyridyl)-1,3-dioxane
  参考文献：
  名称：

  Pyridine derivatives

  摘要：

  本发明涉及一类新型的、具有药物活性的1,3-二氧杂环戊烷烯酸衍生物，其通式为I，其中二氧杂环戊烷环的第4位含有吡啶基团，且第2、4和5位的基团具有顺式相对立体化学结构，X是氢、烷氧基或羟基，Y是乙烯基，n是1或2，A.sup.1是亚烷基，二氧杂环戊烷环第2位的取代基R.sup.1和R.sup.2具有多种后续定义的值，而R.sup.4是羟基、生理上可接受的醇残基或烷磺酰胺基，以及它们的药物可接受盐。本发明还包括制造和使用这些酸衍生物的方法，以及用于治疗多种疾病如缺血性心脏病、脑血管病、哮喘病和/或炎症性疾病的药物组合物。

  公开号：

  US05053415A1

文献信息

• US5053415A
  申请人：——

  公开号：US5053415A

  公开（公告）日：1991-10-01
• US5166213A
  申请人：——

  公开号：US5166213A

  公开（公告）日：1992-11-24
• US5248780A
  申请人：——

  公开号：US5248780A

  公开（公告）日：1993-09-28
• US5401849A
  申请人：——

  公开号：US5401849A

  公开（公告）日：1995-03-28
• Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors: Synthesis and Biological Properties of [2-Substituted-4-(3-pyridyl)-1,3-dioxan-5-yl]alkenoic Acids
  作者：Alan W. Faull、Andrew G. Brewster、George R. Brown、Michael J. Smithers、Ruth Jackson

  DOI：10.1021/jm00004a014

  日期：1995.2

  The design, synthesis, and pharmacology of a new class of compounds possessing both thromboxane receptor antagonist and thromboxane synthase inhibitory properties are described. Replacement of the phenol group of the known thromboxane antagonist series 4(Z)-6-[(4RS,5SR)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid by a 3-pyridyl group led to a series of compounds, 5, which were potent thromboxane synthase inhibitors and weak thromboxane antagonists. Further modifications at the dioxane C2 position led to compounds, 7, which were potent dual-acting agents. In the case of compound 7w, the dual activity was shown to reside almost exclusively in the (-)-enantiomer, 7x. Following oral dosing to rats and dogs, 7x (3 mg/kg) displayed significant dual activity over a period of at least 8 h.