3-benzyl-5-methyl-2-(4-methylthiophenyl)-1,3-thiazolidine-4(5H)-one | 1187396-89-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-benzyl-5-methyl-2-(4-methylthiophenyl)-1,3-thiazolidine-4(5H)-one
• CAS: 1187396-89-9
• 化学式: C₁₈H₁₉NOS₂
• 分子量: 329.487
• InChiKey: QGOHHNNYNJXAQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-methyl-2-(4-methylthiophenyl)-1,3-thiazolidine-4(5H)-one 在 双氧水 、 tungsten(VI) oxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以45%的产率得到3-benzyl-5-methyl-2-(4-methylsulfonylphenyl)-1,3-thiazolidine-4(5H)-one
  参考文献：
  名称：

  Design and synthesis of new 2-aryl, 3-benzyl-(1,3-oxazolidine or 1,3-thiazolidine)-4-ones as selective cyclooxygenase (COX-2) inhibitors

  摘要：

  A new series of 2-aryl, 3-benzyl-(1,3-oxazolidine or 1,3-thiazolidine)-4-ones, possessing a methylsulfonyl pharmacophore, were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition studies were performed to acquire structure-activity relationship data with respect to the point that molecular modeling studies showed that designed compounds bind in the primary binding site such that the C-2 para-SO2Me substituent inserts into the 2A degrees pocket present in COX-2 enzyme. COX-1 and COX-2 inhibition studies showed that all compounds were selective inhibitors of the COX-2 isozyme with IC50 values in the highly potent 0.21 to 0.34 mu M range, and COX-2 selectivity indexes in the 222.3 to > 476 range. 3-Benzyl-2-(4-methylsulfonylphenyl)-1,3-oxazolidine-4(5H)-one was identified as the most potent (IC50 = 0.21 mu M) and selective (S.I. > 476) COX-2 inhibitor among the synthesized compounds. It also was a more selective COX-2 inhibitor than the parent reference compound celecoxib (S.I. > 403).

  DOI：

  10.1007/s00044-009-9230-8
• 作为产物：
  描述：

  硫代乳酸 、 4-(甲基巯基)苯甲醛 、 苄胺 以 甲苯 为溶剂， 以35%的产率得到3-benzyl-5-methyl-2-(4-methylthiophenyl)-1,3-thiazolidine-4(5H)-one
  参考文献：
  名称：

  Design and synthesis of new 2-aryl, 3-benzyl-(1,3-oxazolidine or 1,3-thiazolidine)-4-ones as selective cyclooxygenase (COX-2) inhibitors

  摘要：

  A new series of 2-aryl, 3-benzyl-(1,3-oxazolidine or 1,3-thiazolidine)-4-ones, possessing a methylsulfonyl pharmacophore, were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition studies were performed to acquire structure-activity relationship data with respect to the point that molecular modeling studies showed that designed compounds bind in the primary binding site such that the C-2 para-SO2Me substituent inserts into the 2A degrees pocket present in COX-2 enzyme. COX-1 and COX-2 inhibition studies showed that all compounds were selective inhibitors of the COX-2 isozyme with IC50 values in the highly potent 0.21 to 0.34 mu M range, and COX-2 selectivity indexes in the 222.3 to > 476 range. 3-Benzyl-2-(4-methylsulfonylphenyl)-1,3-oxazolidine-4(5H)-one was identified as the most potent (IC50 = 0.21 mu M) and selective (S.I. > 476) COX-2 inhibitor among the synthesized compounds. It also was a more selective COX-2 inhibitor than the parent reference compound celecoxib (S.I. > 403).

  DOI：

  10.1007/s00044-009-9230-8