(Z)-5-fluoro-3-(3'-methoxy-4'-(2-oxo-2-(piperidin-1-yl)ethoxy)benzylidene)indolin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-5-fluoro-3-(3'-methoxy-4'-(2-oxo-2-(piperidin-1-yl)ethoxy)benzylidene)indolin-2-one
• 英文别名: (3Z)-5-fluoro-3-[[3-methoxy-4-(2-oxo-2-piperidin-1-ylethoxy)phenyl]methylidene]-1H-indol-2-one
• 化学式: C₂₃H₂₃FN₂O₄
• 分子量: 410.445
• InChiKey: ACVCUPRABZBKOV-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-氯-1-哌啶-1-基乙酮 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 (Z)-5-fluoro-3-(3'-methoxy-4'-(2-oxo-2-(piperidin-1-yl)ethoxy)benzylidene)indolin-2-one
  参考文献：
  名称：

  Design, synthesis and apoptosis inducing effect of novel (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones as potential antitumour agents

  摘要：

  A series of new (Z)-3-(3'-methoxy-4'-(2-amino-2-oxoethoxy)benzylidene)indolin-2-one derivatives has been synthesized and evaluated for their cytotoxic activity against selected human cancer cell lines of prostate (PC-3 and DU-145), breast (BT-549 and MDA-MB-231) and non-tumorigenic prostate epithelial cells (RWPE-1). Among the tested, one of the compounds 4p exhibited potent cytotoxicity selectively on prostate cancer cell lines (PC-3 and DU-145; IC50: 1.89 +/- 0.6 and 1.94 +/- 0.2 mu M, respectively). Further experiments were conducted with 4p on PC-3 cancer cells to study the mechanisms of growth inhibition and apoptosis inducing effect. Treatment of PC-3 cells with test compound 4p resulted in inhibition of cell migration through disorganization of F-actin protein. The flow-cytometry analysis results showed that the compound arrested PC-3 cancer cells in the G2/M phase of cell cycle in a dose dependent manner. Hoechst staining and annexin-V binding assay revealed that the compound 4p inhibited tumor cell proliferation through induction of apoptosis. Western blot studies demonstrated that the compound 4p treatment led to activation of caspase-3, increased, expression of pro-apoptotic Bax and significantly decreased expression of anti-apoptotic Bcl-2 in human prostate cancer PC-3 cells. In addition, the mitochondrial membrane potential (Delta Psi m) was also affected and the levels of intracellular Ca2+ were raised. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.025

文献信息

• Design, synthesis and apoptosis inducing effect of novel (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones as potential antitumour agents
  作者：Kishna Ram Senwar、T. Srinivasa Reddy、Dinesh Thummuri、Pankaj Sharma、V.G.M. Naidu、Gannoju Srinivasulu、Nagula Shankaraiah

  DOI：10.1016/j.ejmech.2016.04.025

  日期：2016.8

  A series of new (Z)-3-(3'-methoxy-4'-(2-amino-2-oxoethoxy)benzylidene)indolin-2-one derivatives has been synthesized and evaluated for their cytotoxic activity against selected human cancer cell lines of prostate (PC-3 and DU-145), breast (BT-549 and MDA-MB-231) and non-tumorigenic prostate epithelial cells (RWPE-1). Among the tested, one of the compounds 4p exhibited potent cytotoxicity selectively on prostate cancer cell lines (PC-3 and DU-145; IC50: 1.89 +/- 0.6 and 1.94 +/- 0.2 mu M, respectively). Further experiments were conducted with 4p on PC-3 cancer cells to study the mechanisms of growth inhibition and apoptosis inducing effect. Treatment of PC-3 cells with test compound 4p resulted in inhibition of cell migration through disorganization of F-actin protein. The flow-cytometry analysis results showed that the compound arrested PC-3 cancer cells in the G2/M phase of cell cycle in a dose dependent manner. Hoechst staining and annexin-V binding assay revealed that the compound 4p inhibited tumor cell proliferation through induction of apoptosis. Western blot studies demonstrated that the compound 4p treatment led to activation of caspase-3, increased, expression of pro-apoptotic Bax and significantly decreased expression of anti-apoptotic Bcl-2 in human prostate cancer PC-3 cells. In addition, the mitochondrial membrane potential (Delta Psi m) was also affected and the levels of intracellular Ca2+ were raised. (C) 2016 Elsevier Masson SAS. All rights reserved.