3-(4-Chloroanilino)-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione | 1322705-20-3

• 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: 3-(4-Chloroanilino)-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione
• CAS: 1322705-20-3
• 化学式: C₂₂H₁₇ClN₂O₄
• 分子量: 408.841
• InChiKey: RBIWLKASEDRUNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-hydroxy-2-(4-phenoxyphenyl)propionate 在 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 3-(4-Chloroanilino)-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione
  参考文献：
  名称：

  Design, syntheses, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors

  摘要：

  The cytochrome bc(1) complex (EC 1.10.2.2, bc(1)) is one of the most promising targets for new drugs and agricultural fungicides. Among the existing bc(1) complex inhibitors specifically binding to the Q(o) site, oxazolidinedione derivatives have attracted great attention. With the aim to understand the substituent effects of oxazolidinedione derivatives on the inhibition activity against the bc(1) complex, a series of new oxazolidinedione derivatives were designed, synthesized, and biologically evaluated. The further inhibitory kinetics studies against porcine succinate-cytochrome c reductase (SCR) revealed that the representative compound 8d and famoxadone are both non-competitive inhibitors with respect to the substrate cytochrome c, but competitive inhibitors with respect to substrate decylubiquinol (DBH2). In addition, compound 8d and famoxadone showed, respectively, 35-fold and 15-fold greater inhibitory activity against the porcine SCR than the porcine bc(1) complex, indicating that these two inhibitors not only inhibited the activity of the bc(1) complex, but possibly affect the interaction between the complex II and the bc(1) complex. To our knowledge, this is the first report that famoxadone and its analogs have effects on the interaction between the complex II and the bc(1) complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.008

文献信息

• Design, syntheses, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors
  作者：Fu Wang、Hui Li、Le Wang、Wen-Chao Yang、Jia-Wei Wu、Guang-Fu Yang

  DOI：10.1016/j.bmc.2011.06.008

  日期：2011.8

  The cytochrome bc(1) complex (EC 1.10.2.2, bc(1)) is one of the most promising targets for new drugs and agricultural fungicides. Among the existing bc(1) complex inhibitors specifically binding to the Q(o) site, oxazolidinedione derivatives have attracted great attention. With the aim to understand the substituent effects of oxazolidinedione derivatives on the inhibition activity against the bc(1) complex, a series of new oxazolidinedione derivatives were designed, synthesized, and biologically evaluated. The further inhibitory kinetics studies against porcine succinate-cytochrome c reductase (SCR) revealed that the representative compound 8d and famoxadone are both non-competitive inhibitors with respect to the substrate cytochrome c, but competitive inhibitors with respect to substrate decylubiquinol (DBH2). In addition, compound 8d and famoxadone showed, respectively, 35-fold and 15-fold greater inhibitory activity against the porcine SCR than the porcine bc(1) complex, indicating that these two inhibitors not only inhibited the activity of the bc(1) complex, but possibly affect the interaction between the complex II and the bc(1) complex. To our knowledge, this is the first report that famoxadone and its analogs have effects on the interaction between the complex II and the bc(1) complex. (C) 2011 Elsevier Ltd. All rights reserved.