1-(2,6-dichlorophenyl)-3-(3-bromobenzylidene)-1,3-dihydroindol-2-one | 1146981-17-0

• 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: 1-(2,6-dichlorophenyl)-3-(3-bromobenzylidene)-1,3-dihydroindol-2-one
• 英文别名: 3-[(3-bromophenyl)methylidene]-1-(2,6-dichlorophenyl)indol-2-one
• CAS: 1146981-17-0
• 化学式: C₂₁H₁₂BrCl₂NO
• 分子量: 445.142
• InChiKey: SXNFLNBXOVNKIF-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151 °C(Solvent: Methanol)
• 沸点：
  556.4±50.0 °C(predicted)
• 密度：
  1.600±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2,6-二氯-N-苯基苯胺 在 哌啶 、 aluminum (III) chloride 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 1-(2,6-dichlorophenyl)-3-(3-bromobenzylidene)-1,3-dihydroindol-2-one
  参考文献：
  名称：

  In vitro cytotoxicity evaluation of diversely substituted N-aryl-2-oxindoles

  摘要：

  In continuation with our previous work, structurally diverse 2-indolinones bearing 2,6-dichloroaryl fragment at N (1) and (hetero)aryl benzylidene at C-3 were evaluated for their antitumor activity on a panel of cancer cell lines such as MCF-7 (breast), MiapaCa2 (pancreas), KB (oral), HuTu80 (stomach), L132 (lung), B16F10 (melanoma), and Molt4 (leukemia) from various human organs. Among the screened compound library, molecules 4e, 4k, and 4r have shown excellent cytotoxicity on a stomach cancer cell line. Moreover, a significant number of compounds have also shown promising cytotoxicity on pancreas and oral cancer cell lines.

  DOI：

  10.1007/s00044-012-0309-2

文献信息

• Synthesis of 1-(2,6-dichlorophenyl)-3-methylene-1,3-dihydro-indol-2-one derivatives and in vitro anticancer evaluation against SW620 colon cancer cell line
  作者：Vijay Virsodia、Atul Manvar、Kuldip Upadhyay、Rajesh Loriya、Denish Karia、Manu Jaggi、Anu Singh、Rama Mukherjee、Mushtaque S. Shaikh、Evans C. Coutinho

  DOI：10.1016/j.ejmech.2008.01.012

  日期：2009.3

  A small library of 2-indolinane derivatives with the 2,6-dichlorophenyl ring at the N-1 position and with varying substitutions including aryl groups at the 3-position were synthesized, and their structures were confirmed by spectral analysis. All molecules were screened for their in vitro cytotoxic activity on SW620 colon cancer cell lines. Among the designed series compounds 4c, 4f and 4j were found to be active at concentrations of 2-15 mu g/ml. Some 3D-QSAR models were also built to understand the structure-activity relationship, (C) 2008 Elsevier Masson SAS. All rights reserved.