(Z)-6-[(2S,4S,5R)-2-(4-Cyano-phenyl)-4-pyridin-3-yl-[1,3]dioxan-5-yl]-hex-4-enoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-6-[(2S,4S,5R)-2-(4-Cyano-phenyl)-4-pyridin-3-yl-[1,3]dioxan-5-yl]-hex-4-enoic acid
• 英文别名: (Z)-6-[(2S,4S,5R)-2-(4-cyanophenyl)-4-pyridin-3-yl-1,3-dioxan-5-yl]hex-4-enoic acid
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: NXCNRQBBNYHOOQ-WMUKYIDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-6-[(2S,4S,5R)-2-(4-Cyano-phenyl)-4-pyridin-3-yl-[1,3]dioxan-5-yl]-hex-4-enoic acid 在 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (Z)-6-[(2S,4S,5R)-2-(4-Cyano-phenyl)-4-pyridin-3-yl-[1,3]dioxan-5-yl]-hex-4-enoic acid 6-hydroxy-hexyl ester
  参考文献：
  名称：

  Design of dual-acting thromboxane antagonist-synthase inhibitors by a mutual prodrug approach

  摘要：

  A mutual prodrug approach to dual acting thromboxane receptor antagonist - thromboxane synthase inhibitor compounds is reported in which TXA(2) antagonist and inhibitory 19-dioxanes with hexenoic acid side chains, were linked by diester and diamide groups. When linking of the components was achieved via di O-alkyl carboxylic esters of catechol, both TXA(2) receptor antagonist activity and TXA(2) synthase inhibition were observed for a single enantiomer (16) in ex vivo tests following oral dosing to dogs at 5 mg/kg.

  DOI：

  10.1016/0960-894x(96)00004-2
• 作为产物：
  描述：

  4-氰基苯甲醛 、 4(Z)-6-cis-<2,2-dimethyl-4-(3-pyridyl)-1,3-dioxan-5-yl>hexenoic acid 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以60%的产率得到(Z)-6-[(2S,4S,5R)-2-(4-Cyano-phenyl)-4-pyridin-3-yl-[1,3]dioxan-5-yl]-hex-4-enoic acid
  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