2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid | 681454-59-1

• 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: 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid
• 英文别名: 2-(4-Methylsulfonylphenyl)cyclopentene-1-carboxylic acid
• CAS: 681454-59-1
• 化学式: C₁₃H₁₄O₄S
• 分子量: 266.318
• InChiKey: WTTRLRKDZFFJJG-UHFFFAOYSA-N

物化性质

• 沸点：
  470.2±45.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯胺 、 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以30%的产率得到2-(4-methylsulfonylphenyl)-N-phenylcyclopentene-1-carboxamide
  参考文献：
  名称：

  Synthesis and COX-2 inhibitory properties of N-phenyl- and N-benzyl-substituted amides of 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid and of their pyrazole, thiophene and isoxazole analogs

  摘要：

  Some N-phenyl- (7a-10a) and N-benzyl-substituted (7b-10b) amido analogs of cyclooxygenase (COX-2) selective tricyclic non-steroidal anti-inflammatory drugs have been synthesized with the aim to obtain information on the structural requirements for the COX-inhibitory activity. Compounds 7-10 were tested in vitro for their inhibitory properties only towards COX-2 enzyme by measuring prostaglandin E2 (PGE2) production on activated J774.2 macrophages. Some of the new compounds (7a, 8a, 9a and 9b) showed a modest activity, with percentage inhibition values near 30% at a concentration of 10 microM. These data have been tentatively explained by a conformational study which indicates that at least the N-phenyl-substituted amides 7a-9a present steric hindrances which may prevent a good interaction with COX-2 active site.

  DOI：

  10.1016/j.farmac.2003.09.003
• 作为产物：
  描述：

  2-溴环戊烯-1-甲醛 在 四(三苯基膦)钯 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 17.0h， 生成 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid
  参考文献：
  名称：

  Synthesis and COX-2 inhibitory properties of N-phenyl- and N-benzyl-substituted amides of 2-(4-methylsulfonylphenyl)cyclopent-1-ene-1-carboxylic acid and of their pyrazole, thiophene and isoxazole analogs

  摘要：

  Some N-phenyl- (7a-10a) and N-benzyl-substituted (7b-10b) amido analogs of cyclooxygenase (COX-2) selective tricyclic non-steroidal anti-inflammatory drugs have been synthesized with the aim to obtain information on the structural requirements for the COX-inhibitory activity. Compounds 7-10 were tested in vitro for their inhibitory properties only towards COX-2 enzyme by measuring prostaglandin E2 (PGE2) production on activated J774.2 macrophages. Some of the new compounds (7a, 8a, 9a and 9b) showed a modest activity, with percentage inhibition values near 30% at a concentration of 10 microM. These data have been tentatively explained by a conformational study which indicates that at least the N-phenyl-substituted amides 7a-9a present steric hindrances which may prevent a good interaction with COX-2 active site.

  DOI：

  10.1016/j.farmac.2003.09.003