2-[(Z)-4-[5-[2-(4-bromophenyl)ethynyl]-2,4-dioxopyrimidin-1-yl]but-2-enyl]isoindole-1,3-dione | 1040562-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[(Z)-4-[5-[2-(4-bromophenyl)ethynyl]-2,4-dioxopyrimidin-1-yl]but-2-enyl]isoindole-1,3-dione
• CAS: 1040562-90-0
• 化学式: C₂₄H₁₆BrN₃O₄
• 分子量: 490.313
• InChiKey: PQSYKAJEWQRKDN-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-溴苯基)乙炔 、 (Z)-1-[4'-phthalimido-2'-butenyl]-5-iodouracil 在 四(三苯基膦)钯 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以61.6%的产率得到2-[(Z)-4-[5-[2-(4-bromophenyl)ethynyl]-2,4-dioxopyrimidin-1-yl]but-2-enyl]isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues

  摘要：

  A series of the novel C-5 alkynyl pyrimidine nucleoside analogues (1-14) in which the sugar moiety was replaced by the conformationally restricted Z- and E-2-butenyl spacer between the phthalimido and pyrimidine ring were synthesized by using Sonogashira cross-coupling reaction. Cytostatic activity evaluation of the novel compounds showed that E-isomers exhibited, in general, better cytostatic activities than the corresponding Z-isomers. E-isomer 14 exhibited the best cytostatic effect against all evaluated malignant cell lines, particularly against hepatocellular carcinoma (Hep G2, IC50 = 4.3 mu M). However, this compound was also cytotoxic to human normal fibroblasts (WI 38). Its Z-isomer 7 showed highly specific antiproliferative activity against Hep G2 (IC50 = 18 mu M) and no cytotoxicity to WI 38. Moreover, compounds 3, 4 and 14 expressed some marginal inhibitory activity against HIV-1 and HIV-2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.074

文献信息

• Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues
  作者：Tatjana Gazivoda、Silvana Raić-Malić、Vedran Krištafor、Damjan Makuc、Janez Plavec、Siniša Bratulić、Sandra Kraljević-Pavelić、Krešimir Pavelić、Lieve Naesens、Graciela Andrei、Robert Snoeck、Jan Balzarini、Mladen Mintas

  DOI：10.1016/j.bmc.2008.03.074

  日期：2008.5

  A series of the novel C-5 alkynyl pyrimidine nucleoside analogues (1-14) in which the sugar moiety was replaced by the conformationally restricted Z- and E-2-butenyl spacer between the phthalimido and pyrimidine ring were synthesized by using Sonogashira cross-coupling reaction. Cytostatic activity evaluation of the novel compounds showed that E-isomers exhibited, in general, better cytostatic activities than the corresponding Z-isomers. E-isomer 14 exhibited the best cytostatic effect against all evaluated malignant cell lines, particularly against hepatocellular carcinoma (Hep G2, IC50 = 4.3 mu M). However, this compound was also cytotoxic to human normal fibroblasts (WI 38). Its Z-isomer 7 showed highly specific antiproliferative activity against Hep G2 (IC50 = 18 mu M) and no cytotoxicity to WI 38. Moreover, compounds 3, 4 and 14 expressed some marginal inhibitory activity against HIV-1 and HIV-2. (C) 2008 Elsevier Ltd. All rights reserved.