N-methyl-2-(3-(2-(2-(3-(2-nitro-1H-imidazol-1-yl)propanoyl)hydrazine-1-carbonothioyl)hydrazineylidene)butan-2-ylidene)hydrazine-1-carbothioamide | 1208998-90-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-methyl-2-(3-(2-(2-(3-(2-nitro-1H-imidazol-1-yl)propanoyl)hydrazine-1-carbonothioyl)hydrazineylidene)butan-2-ylidene)hydrazine-1-carbothioamide
• CAS: 1208998-90-6
• 化学式: C₁₃H₂₀N₁₀O₃S₂
• 分子量: 428.499
• InChiKey: ICHGPVRVPBCYOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  162.9
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  diacetyl-2-(4-N-methyl-3-thiosemicarbazone)-3-(4-N-amino-3-thiosemicarbazone) 、 3-(2-nitro-1H-imidazolyl)propionic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 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 12.0h， 以81%的产率得到N-methyl-2-(3-(2-(2-(3-(2-nitro-1H-imidazol-1-yl)propanoyl)hydrazine-1-carbonothioyl)hydrazineylidene)butan-2-ylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Nitroimidazole conjugates of bis(thiosemicarbazonato)64Cu(II) – Potential combination agents for the PET imaging of hypoxia

  摘要：

  Combination agents comprising two different pharmacophores with the same biological target have the potential to show additive or synergistic activity. Bis(thiosemicarbazonato)copper(II) complexes (e.g. Cu-64-ATSM) and nitroimidazoles (e.g. F-18-MISO) are classes of tracer used for the delineation of tumor hypoxia by positron emission tomography (PET). Three nitroimidazole-bis(thiosemicarbazonato)copper(II) conjugates were produced in order to investigate their potential as combination hypoxia imaging agents. Two were derived from the known bifunctional bis(thiosemicarbazone) H(2)ATSM/A and the third from the new precursor diacetyl-2-(4-N-methyl-3-thiosemicarbazone)-3-(4-N-ethylamino-3-thiosemicarbazone) - H(2)ATSM/en. Oxygen-dependent uptake studies were performed using the Cu-64 radiolabelled complexes in EMT6 carcinoma cells. All the complexes displayed appreciable hypoxia selectivity, with the nitroimidazole conjugates displaying greater selectivity than a simple propyl derivative used as a control. Participation of the nitroimidazole group in the trapping mechanism is indicated by the increased hypoxic uptake of the 2- vs. the 4-substituted Cu-64-ATSM/A derivatives. The 2-nitroimidazole derivative of Cu-64-ATSM/en demonstrated superior hypoxia selectivity to Cu-64-ATSM over the range of oxygen concentrations tested. Biodistribution of the radiolabelled 2-nitroimidazole conjugates was carried out in EMT6 tumor-bearing mice. The complexes showed significantly different uptake trends in comparison to each other and previously studied Cu-ATSM derivatives. Uptake of the Cu-ATSM/en conjugate in non-target organs was considerably lower than for derivatives based on Cu-ATSM/A. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2009.10.009