Succinic acid mono-[1-(2-nitro-imidazol-1-ylmethyl)-5-(4-nitro-phenylsulfanyl)-pent-3-ynyl] ester | 710337-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Succinic acid mono-[1-(2-nitro-imidazol-1-ylmethyl)-5-(4-nitro-phenylsulfanyl)-pent-3-ynyl] ester
• CAS: 710337-21-6
• 化学式: C₁₉H₁₈N₄O₈S
• 分子量: 462.44
• InChiKey: YPKTXYRHZBKDBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  167.7
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Succinic acid mono-[1-(2-nitro-imidazol-1-ylmethyl)-5-(4-nitro-phenylsulfanyl)-pent-3-ynyl] ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到4-[1-(2-Nitroimidazol-1-yl)-6-(4-nitrophenyl)sulfonylhex-4-yn-2-yl]oxy-4-oxobutanoic acid
  参考文献：
  名称：

  Propargylic sulfones possessing a 2-nitroimidazole function: novel hypoxic-cell radiosensitizers with intracellular non-protein thiol depletion ability

  摘要：

  Propargylic sulfones (1a-c) containing a 2-nitroimidazole structure were synthesized, and their non-protein thiol (NPSH) depletion abilities were investigated. Propargylic sulfones la,c containing an electron withdrawing p-nitrophenyl group showed high reactivity toward capturing glutathione (GSH), a typical intracellular NPSH, in phosphate buffer. Among the three propargylic sulfones 1a-c, carboxylic acid derivative 1c showed the most potent radiosensitizing activity toward hypoxic EMT6/KU tumor cells. In view of these results and the partition coefficients between 1-octanol and water, we concluded that appropriate NPSH-depletion ability and lipophilicity are both important in achieving potent hypoxic-cell radiosensitization by propargylic sulfones possessing a 2-nitroimidazole function in biological systems. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.060
• 作为产物：
  描述：

  2-[4-(oxiran-2-yl)but-2-ynoxy]oxane 在 甲醇 、 4-二甲氨基吡啶 、 sodium hydroxide 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 Succinic acid mono-[1-(2-nitro-imidazol-1-ylmethyl)-5-(4-nitro-phenylsulfanyl)-pent-3-ynyl] ester
  参考文献：
  名称：

  Propargylic sulfones possessing a 2-nitroimidazole function: novel hypoxic-cell radiosensitizers with intracellular non-protein thiol depletion ability

  摘要：

  Propargylic sulfones (1a-c) containing a 2-nitroimidazole structure were synthesized, and their non-protein thiol (NPSH) depletion abilities were investigated. Propargylic sulfones la,c containing an electron withdrawing p-nitrophenyl group showed high reactivity toward capturing glutathione (GSH), a typical intracellular NPSH, in phosphate buffer. Among the three propargylic sulfones 1a-c, carboxylic acid derivative 1c showed the most potent radiosensitizing activity toward hypoxic EMT6/KU tumor cells. In view of these results and the partition coefficients between 1-octanol and water, we concluded that appropriate NPSH-depletion ability and lipophilicity are both important in achieving potent hypoxic-cell radiosensitization by propargylic sulfones possessing a 2-nitroimidazole function in biological systems. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.060