N,N'-bis-{3-[2,5-dioxo-3,4-di(thien-2-yl)-1H-pyrrol-1-yl]propyl}-piperazine | 1338339-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N,N'-bis-{3-[2,5-dioxo-3,4-di(thien-2-yl)-1H-pyrrol-1-yl]propyl}-piperazine
• 英文别名: 1-[3-[4-[3-(2,5-Dioxo-3,4-dithiophen-2-ylpyrrol-1-yl)propyl]piperazin-1-yl]propyl]-3,4-dithiophen-2-ylpyrrole-2,5-dione
• CAS: 1338339-48-2
• 化学式: C₃₄H₃₂N₄O₄S₄
• 分子量: 688.916
• InChiKey: XGEGCTYXCIFNEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  194
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 3,4-(二-噻吩-2-基)呋喃-2,5-二酮 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到N,N'-bis-{3-[2,5-dioxo-3,4-di(thien-2-yl)-1H-pyrrol-1-yl]propyl}-piperazine
  参考文献：
  名称：

  Synthesis, structural, and biological evaluation of bis-heteroarylmaleimides and bis-heterofused imides

  摘要：

  Bis-2,3-heteroarylmaleimides and polyheterocondensed imides joined through nitrogen atoms of the N, N'-bis(ethyl)-1,3-propanediamine linker were prepared from substituted maleic anhydrides and symmetrical diamines in good to satisfactory yields and short reaction times using microwave heating. The novel molecules were shown to inhibit proliferation of human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs) with variable potencies. Compound 11a, the most potent one of the series, showed IC50 values comparable to those observed for the leading molecule elinafide in both cell lines, but with a higher selectivity toward human tumor cells. Compound 11a affected G1/S phase transition of the cell cycle, showed in vitro DNA intercalating activity and in vivo antitumor activity. A thorough structural analysis of the 11a-DNA complex was also made by mean of NMR and computational techniques. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.016

文献信息

• Synthesis, structural, and biological evaluation of bis-heteroarylmaleimides and bis-heterofused imides
  作者：Nicola Ferri、Tiziano Radice、Manuela Antonino、Egle Maria Beccalli、Stella Tinelli、Franco Zunino、Alberto Corsini、Graziella Pratesi、Enzio M. Ragg、Maria Luisa Gelmi、Alessandro Contini

  DOI：10.1016/j.bmc.2011.08.016

  日期：2011.9

  Bis-2,3-heteroarylmaleimides and polyheterocondensed imides joined through nitrogen atoms of the N, N'-bis(ethyl)-1,3-propanediamine linker were prepared from substituted maleic anhydrides and symmetrical diamines in good to satisfactory yields and short reaction times using microwave heating. The novel molecules were shown to inhibit proliferation of human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs) with variable potencies. Compound 11a, the most potent one of the series, showed IC50 values comparable to those observed for the leading molecule elinafide in both cell lines, but with a higher selectivity toward human tumor cells. Compound 11a affected G1/S phase transition of the cell cycle, showed in vitro DNA intercalating activity and in vivo antitumor activity. A thorough structural analysis of the 11a-DNA complex was also made by mean of NMR and computational techniques. (C) 2011 Elsevier Ltd. All rights reserved.