methyl 4-(mercaptomethyl)-3-methoxybenzoate | 112682-05-0

• 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 4-(mercaptomethyl)-3-methoxybenzoate
• 英文别名: Methyl 3-methoxy-4-mercaptomethylbenzoate；Methyl 3-methoxy-4-(sulfanylmethyl)benzoate
• CAS: 112682-05-0
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: NBOLTMKGZKSXMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(mercaptomethyl)-3-methoxybenzoate 在 lithium hydroxide 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 22.0h， 生成 (5S,6R,7Z)-6-<<(4-carboxy-2-methoxyphenyl)methyl>thio>-5-hydroxy-9-(4-heptylphenyl)-7-nonenoic acid dilithium salt
  参考文献：
  名称：

  Synthesis and pharmacological characterization of a series of leukotriene analogs with antagonist and agonist activities

  摘要：

  The synthesis and biological characterization of a series of novel leukotriene antagonists and agonists are reported. All of these compounds are derivatives of (5S,6R,7Z)-5-hydroxy-6-mercapto-9-phenyl-7-nonenoic acid. One of the more potent compounds is (5S,6R,7Z)-6-[[(4-carboxy-2-methoxyphenyl)methyl]thio]-5-hydroxy-9 -(4- heptylphenyl)-7-nonenoic acid (3f). In vitro evaluation of this compound on guinea pig trachea revealed that it is a competitive antagonist of LTD4 and LTE4 with pKB values of 6.4 and 5.8, respectively. On guinea pig ileum, the pKB values obtained for it with LTD4 and E4 were both 7.2. The selectivity of 3f was shown by its lack of effect on carbachol, histamine, and barium chloride concentration-response curves in guinea pig trachea.

  DOI：

  10.1021/jm00398a033
• 作为产物：
  描述：

  4-溴甲基-3-甲氧基苯甲酸甲酯 在 potassium carbonate 、 硫代乙酸 作用下， 以 甲醇 为溶剂， 以66%的产率得到methyl 4-(mercaptomethyl)-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis and pharmacological characterization of a series of leukotriene analogs with antagonist and agonist activities

  摘要：

  The synthesis and biological characterization of a series of novel leukotriene antagonists and agonists are reported. All of these compounds are derivatives of (5S,6R,7Z)-5-hydroxy-6-mercapto-9-phenyl-7-nonenoic acid. One of the more potent compounds is (5S,6R,7Z)-6-[[(4-carboxy-2-methoxyphenyl)methyl]thio]-5-hydroxy-9 -(4- heptylphenyl)-7-nonenoic acid (3f). In vitro evaluation of this compound on guinea pig trachea revealed that it is a competitive antagonist of LTD4 and LTE4 with pKB values of 6.4 and 5.8, respectively. On guinea pig ileum, the pKB values obtained for it with LTD4 and E4 were both 7.2. The selectivity of 3f was shown by its lack of effect on carbachol, histamine, and barium chloride concentration-response curves in guinea pig trachea.

  DOI：

  10.1021/jm00398a033

文献信息

• Leukotriene antagonists
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0296732B1

  公开（公告）日：1991-10-09
• BERNSTEIN, PETER R.;VACEK, EDWARD P.;ADAMS, EDWARD J.;SNYDER, DAVID W.;KR+, J. MED. CHEM., 31,(1988) N 3, 692-696
  作者：BERNSTEIN, PETER R.、VACEK, EDWARD P.、ADAMS, EDWARD J.、SNYDER, DAVID W.、KR+

  DOI：——

  日期：——
• US5314918A
  申请人：——

  公开号：US5314918A

  公开（公告）日：1994-05-24