methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(pyridin-3-yl)-6-heptenoate | 92571-24-9

• 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: methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(pyridin-3-yl)-6-heptenoate
• 英文别名: methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate；Methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate；methyl (E)-2-(2-hydroxypropan-2-yl)-7-phenyl-7-pyridin-3-ylhept-6-enoate
• CAS: 92571-24-9
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: OCWDNCZUHZFEMB-CPNJWEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碳酸氢钠 、 methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(pyridin-3-yl)-6-heptenoate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (E)-2-(1-methylethenyl)-7-phenyl-7-(pyridin-3-yl)-6-heptenoate
  参考文献：
  名称：

  Vinyl carboxylic acid derivatives, their production and use as

  摘要：

  式（I）的新化合物：##STR1## 其中R1是吡啶基团；R2是苯基、噻吩基、呋喃基、萘基、苯并噻吩基或吡啶基团，其上可带有取代基，如低级烷氧基、低级烷基、卤素、三氟甲基、低级链烯基或亚甲二氧基；R3是氢、苄基或低级烷基；R4和R5中之一是氢或低级烷基，另一是芳氧基、低级脂肪族烃、不超过6个碳原子的脂环烃或芳香基团，该芳香基团可带有取代基，或由式--S(O)m--R6表示的基团（其中R6是苯基或低级烷基团；m是0至2的整数），或者R4和R5各自与其他基团结合形成一个亚烷基团；n是2至6的整数，或其药学上可接受的盐，具有选择性抑制血栓素A2（TXA2）生物合成和增强前列环素I2（PGI2）产生的作用，可用于哺乳动物预防和治疗由血小板聚集引起的动脉血栓形成或由血管痉挛引起的心脏、脑和外周循环系统的缺血性疾病（例如心肌梗死、中风、肾脏、肺和其他器官的血管梗死、消化性溃疡等）。

  公开号：

  US04518602A1
• 作为产物：
  描述：

  丙酮 、 methyl (E)-7-phenyl-7-(3-pyridyl)-6-heptenoate 在 lithium diisopropyl amide 作用下， 生成 methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(pyridin-3-yl)-6-heptenoate
  参考文献：
  名称：

  Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of .omega.-pyridylalkenoic acids

  摘要：

  A novel series of omega-pyridylalkenoic acids has been prepared by applying the Wittig reaction. Modifications were made in the omega-aryl moiety, the alkylene chain length, the alpha-methylene group adjacent to the carbonyl group, and the carboxyl group of the molecule. The compounds were tested as inhibitors of thromboxane synthetase in an in vitro assay and in ex vivo experiments with the rat. Most members of this new class of thromboxane synthetase inhibitors (TXSI) showed good activity in both assay systems. (E)-7-Phenyl-7-(3-pyridyl)-6-heptenoic acid (9c; CV-4151) was one of the most potent compounds in in vitro enzyme inhibition (IC50 = 2.6 X 10(-8) M) and, when orally administered, the most potent and long acting in the inhibition of blood thromboxane A2 production in the rat. New conceptual models I-III for the enzyme-substrate (prostaglandin H2, PGH2) and the enzyme-TXSI interactions are proposed for understanding the molecular design and structure-activity relations.

  DOI：

  10.1021/jm00381a005