(3R,4'R)-1',3',4'-triphenylspiro[1H-indole-3,5'-4H-pyrazole]-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: (3R,4'R)-1',3',4'-triphenylspiro[1H-indole-3,5'-4H-pyrazole]-2-one
• 化学式: C₂₈H₂₁N₃O
• 分子量: 415.494
• InChiKey: YJVZHGQFCSMIEF-LSYYVWMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛苯腙 在 N-chlorosuccinimide-dimethylsulfide complex 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R,4'R)-1',3',4'-triphenylspiro[1H-indole-3,5'-4H-pyrazole]-2-one
  参考文献：
  名称：

  Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines

  摘要：

  A series of novel spiropyrazoline oxindole derivatives was synthesized by 1,3-dipolar cycloaddition reaction. The compounds were screened for their in vitro cytotoxic activity against MCF-7 breast cancer cell line (estrogen receptor positive (ER+) and human epidermal growth factor receptor 2 negative (HER2-)). Of the nineteen spiropyrazoline oxindoles tested, six compounds have a GI(50) below 12 mu M The most potent compounds in this series were also evaluated against MDA-MB-231 breast cancer cell line (ER and HER2-). Two spiropyrazoline oxindoles were highly selective between MCF-7 tumor cells and MDA-MB-231 tumor cells. More importantly, they were noncytotoxic against HER 293T non tumor derived cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.023

文献信息

• In vitro targeting of colon cancer cells using spiropyrazoline oxindoles
  作者：Rute C. Nunes、Carlos J.A. Ribeiro、Ângelo Monteiro、Cecília M.P. Rodrigues、Joana D. Amaral、Maria M.M. Santos

  DOI：10.1016/j.ejmech.2017.07.057

  日期：2017.10

  We report on the synthesis and biological evaluation of a library of twenty-three spiropyrazoline oxindoles. The antiproliferative activity of the chemical library was evaluated in HCT-116 p53(+/+) human colon cancer cell line with eight derivatives displaying good activities (IC50<15 μM). To characterize the molecular mechanisms involved in compound antitumoral activity, two spiropyrazoline oxindoles

  我们报告了二十三个螺并吡唑啉恶唑的文库的合成和生物学评估。在HCT-116 p53 （+ / +）人结肠癌细胞系中评估了化学文库的抗增殖活性，其中八种衍生物表现出良好的活性（IC 50<15μM）。为了表征参与复合抗肿瘤活性的分子机制，选择了两种螺并吡唑啉恶唑类化合物进行进一步研究。两种化合物均能够诱导细胞凋亡和细胞周期停滞在G0 / G1期并上调p53稳态水平，同时降低其主要抑制剂MDM2。重要的是，螺吡唑啉恶唑诱导的细胞毒性作用在癌细胞中发生，而未引起非恶性CCD-18Co人结肠成纤维细胞的细胞死亡。此外，我们证明了spiropyrazoline oxindole 2e的组合亚毒性浓度的化疗药物5-氟尿嘧啶（5-FU）对HCT-116结肠癌细胞的增殖具有协同抑制作用。总的来说，我们的结果表明螺并吡唑啉恶唑具有开发新型抗癌药的潜力。
• Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines
  作者：Ângelo Monteiro、Lídia M. Gonçalves、Maria M.M. Santos

  DOI：10.1016/j.ejmech.2014.04.023

  日期：2014.5

  A series of novel spiropyrazoline oxindole derivatives was synthesized by 1,3-dipolar cycloaddition reaction. The compounds were screened for their in vitro cytotoxic activity against MCF-7 breast cancer cell line (estrogen receptor positive (ER+) and human epidermal growth factor receptor 2 negative (HER2-)). Of the nineteen spiropyrazoline oxindoles tested, six compounds have a GI(50) below 12 mu M The most potent compounds in this series were also evaluated against MDA-MB-231 breast cancer cell line (ER and HER2-). Two spiropyrazoline oxindoles were highly selective between MCF-7 tumor cells and MDA-MB-231 tumor cells. More importantly, they were noncytotoxic against HER 293T non tumor derived cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.