(E)-2-((2,4-dichlorobenzylidene)amino)-3'-ethoxy-3-oxospiro[isoindoline-1,9'-xanthen]-6'-yl 2-nitrobenzoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-2-((2,4-dichlorobenzylidene)amino)-3'-ethoxy-3-oxospiro[isoindoline-1,9'-xanthen]-6'-yl 2-nitrobenzoate
• 英文别名: [2-[(E)-(2,4-dichlorophenyl)methylideneamino]-6'-ethoxy-3-oxospiro[isoindole-1,9'-xanthene]-3'-yl] 2-nitrobenzoate
• 化学式: C₃₆H₂₃Cl₂N₃O₇
• 分子量: 680.501
• InChiKey: XNNLACCOMGEEPG-JOXMEQDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  fluorescein free acid 在 potassium carbonate 、 一水合肼 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (E)-2-((2,4-dichlorobenzylidene)amino)-3'-ethoxy-3-oxospiro[isoindoline-1,9'-xanthen]-6'-yl 2-nitrobenzoate
  参考文献：
  名称：

  Fluorescein hydrazones: A series of novel non-intercalative topoisomerase IIα catalytic inhibitors induce G1 arrest and apoptosis in breast and colon cancer cells

  摘要：

  Fluorescein hydrazones (5 and 7) were synthesized in three/four steps with 82-92% yields. All synthesized compounds were evaluated by topoisomerase I (topo I) and topoisomerase II alpha (topo II alpha)mediated relaxation and cell viability assays. Among them, most of the compounds showed topo I & II alpha inhibitory activity and nineteen compounds showed strong anti-proliferative activity against various cell lines. In brief, 5e inhibited 53% topo II alpha (etoposide 29%) at 20 mu M and showed excellent antiproliferative activity against DU145 (1.43 +/- 0.04 mu M), HCT15 (2.4 +/- 0.03 mu M) and MCF7 (11.4 +/- 0.5 mu M) cell lines in comparison with adriamycin, etoposide, and camptothecin. Compounds 5e, 5g and 5h were further evaluated to determine their mode of action. Compounds 5e, 5g and 5h functioned as non-intercalative topo II alpha catalytic inhibitor with induction of G1 arrest and activation of apoptotic proteins in dose dependent manner. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.004

文献信息

• Fluorescein hydrazones: A series of novel non-intercalative topoisomerase IIα catalytic inhibitors induce G1 arrest and apoptosis in breast and colon cancer cells
  作者：Mohammad Shahidul Islam、Seojeong Park、Chanju Song、Adnan A. Kadi、Youngjoo Kwon、A.F.M. Motiur Rahman

  DOI：10.1016/j.ejmech.2016.09.004

  日期：2017.1

  Fluorescein hydrazones (5 and 7) were synthesized in three/four steps with 82-92% yields. All synthesized compounds were evaluated by topoisomerase I (topo I) and topoisomerase II alpha (topo II alpha)mediated relaxation and cell viability assays. Among them, most of the compounds showed topo I & II alpha inhibitory activity and nineteen compounds showed strong anti-proliferative activity against various cell lines. In brief, 5e inhibited 53% topo II alpha (etoposide 29%) at 20 mu M and showed excellent antiproliferative activity against DU145 (1.43 +/- 0.04 mu M), HCT15 (2.4 +/- 0.03 mu M) and MCF7 (11.4 +/- 0.5 mu M) cell lines in comparison with adriamycin, etoposide, and camptothecin. Compounds 5e, 5g and 5h were further evaluated to determine their mode of action. Compounds 5e, 5g and 5h functioned as non-intercalative topo II alpha catalytic inhibitor with induction of G1 arrest and activation of apoptotic proteins in dose dependent manner. (C) 2016 Elsevier Masson SAS. All rights reserved.