4'-(4-methoxyphenyl)-3'-phenylspiro[indoline-3,5'-isoxazoline]-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4'-(4-methoxyphenyl)-3'-phenylspiro[indoline-3,5'-isoxazoline]-2-one
• 英文别名: (3R,4'S)-4'-(4-methoxyphenyl)-3'-phenylspiro[1H-indole-3,5'-4H-1,2-oxazole]-2-one
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: VYUXTBHXUWABGF-REWPJTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 50.0h， 生成 4'-(4-methoxyphenyl)-3'-phenylspiro[indoline-3,5'-isoxazoline]-2-one
  参考文献：
  名称：

  Synthesis and evaluation of spiroisoxazoline oxindoles as anticancer agents

  摘要：

  Restoring p53 levels through disruption of p53-MDM2 interaction has been proved to be a valuable approach in fighting cancer. We herein report the synthesis and evaluation of eighteen spiroisoxazoline oxindoles derivatives as p53-MDM2 interaction inhibitors. Seven compounds showed an antiproliferative profile superior to the p53-MDM2 interaction inhibitor nutlin-3, and induced cell death by apoptosis. Moreover, proof-of-concept was demonstrated by inhibition of the interaction between p53 and MDM2 in a live-cell bimolecular fluorescence complementation assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.048

文献信息

• Diastereoselective Synthesis and Structure of Spirooxindole Derivatives
  作者：Francesco Risitano、Giovanni Grassi、Francesco Foti、Giuseppe Bruno、Archimede Rotondo

  DOI：10.3987/com-02-9694

  日期：——

  Spiroindolinonisoxazolines (4 and 5h) are prepared from (E)-1 or (Z)-3-arylidene-2-oxindoles (2) by nitrile oxide cycloaddition reactions. Only one regioisomer is detected in all cases, and the observed complete diastereoselection is established by unambigous structural assignments.
• Synthesis and evaluation of spiroisoxazoline oxindoles as anticancer agents
  作者：Carlos J.A. Ribeiro、Joana D. Amaral、Cecília M.P. Rodrigues、Rui Moreira、Maria M.M. Santos

  DOI：10.1016/j.bmc.2013.10.048

  日期：2014.1

  Restoring p53 levels through disruption of p53-MDM2 interaction has been proved to be a valuable approach in fighting cancer. We herein report the synthesis and evaluation of eighteen spiroisoxazoline oxindoles derivatives as p53-MDM2 interaction inhibitors. Seven compounds showed an antiproliferative profile superior to the p53-MDM2 interaction inhibitor nutlin-3, and induced cell death by apoptosis. Moreover, proof-of-concept was demonstrated by inhibition of the interaction between p53 and MDM2 in a live-cell bimolecular fluorescence complementation assay. (C) 2013 Elsevier Ltd. All rights reserved.