(E)-2-methyl-3-[3-methyl-4-(pyridin-3-ylhydroxymethyl)phenyl]acrylic acid ethyl ester | 75986-40-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-methyl-3-[3-methyl-4-(pyridin-3-ylhydroxymethyl)phenyl]acrylic acid ethyl ester
• 英文别名: (E)-2-methyl-3-[3-methyl-4-(3-pyridylhydroxymethyl)phenyl]acrylic acid ethyl ester；ethyl (E)-3-[4-[hydroxy(pyridin-3-yl)methyl]-3-methylphenyl]-2-methylprop-2-enoate
• CAS: 75986-40-2
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: DQCSMWODGMTKLL-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  (E)-2-methyl-3-[3-methyl-4-(pyridin-3-ylhydroxymethyl)phenyl]acrylic acid ethyl ester 在 氯化亚砜 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006
• 作为产物：
  描述：

  4-溴-3-甲基苯甲醛 在 对甲苯磺酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 19.0h， 生成 (E)-2-methyl-3-[3-methyl-4-(pyridin-3-ylhydroxymethyl)phenyl]acrylic acid ethyl ester
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006

文献信息

• TANOUCHI, TADAO;KAWAMURA, MASANORI;OHYAMA, ISAO;KAJIWARA, IKUO;IGUCHI, YO+, J. MED. CHEM., 1981, 24, N 10, 1149-1155
  作者：TANOUCHI, TADAO、KAWAMURA, MASANORI、OHYAMA, ISAO、KAJIWARA, IKUO、IGUCHI, YO+

  DOI：——

  日期：——
• US4271170A
  申请人：——

  公开号：US4271170A

  公开（公告）日：1981-06-02
• US4317828A
  申请人：——

  公开号：US4317828A

  公开（公告）日：1982-03-02
• US4427682A
  申请人：——

  公开号：US4427682A

  公开（公告）日：1984-01-24