1-(4-nitroimidazole-1-yl)-propanhydroxyiminoamide | 444018-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-nitroimidazole-1-yl)-propanhydroxyiminoamide
• 英文别名: N'-Hydroxy-3-(4-nitro-1H-imidazol-1-yl)propanimidamide；N'-hydroxy-3-(4-nitroimidazol-1-yl)propanimidamide
• CAS: 444018-08-0
• 化学式: C₆H₉N₅O₃
• 分子量: 199.169
• InChiKey: OQAZDPZPAJTCQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sodium [99Tc]pertechnetate 、 1-(4-nitroimidazole-1-yl)-propanhydroxyiminoamide 在 sodium tartrate 、 tin(ll) chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 、
  参考文献：
  名称：

  Preparation and biological evaluation of 99mTc-N4IPA for single photon emission computerized tomography imaging of hypoxia in mouse tumor

  摘要：

  In order to develop technetium-99m labeled nitroimidazole imaging agent for hypoxia in tumor, we have synthesized Tc-99m-1-(4-nitroimidazole-yl)-propanhydroxyiminoamide, Tc-99m-N4IPA complex, in high radiochemical purity and radiochemical yield. The biological evaluation of this complex includes the in vitro/vivo stability, cell uptake and Single Photon Emission Computerized Tomography (SPECT) imaging in mouse tumor models, respectively. These results demonstrate that Tc-99m-N4IPA may have potential as clinical hypoxia imaging agent. The key features of the biological evaluation include the following: (1) the autoradiogram of Tc-99m-N4IPA complex in tissue samples of hypoxia overlaps with the area stained by hypoxyprobe-1; (2) SPED' imaging of U87-bearing mice clearly identifies tumors 4 h post injection of Tc-99m-N4IPA, reaching ID% of 8.48 +/- 4.51; (3) the main pathways of excretion of Tc-99m-N4IPA are through kidneys and livers in both A549 or U87-bearing tumor mice. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.005
• 作为产物：
  描述：

  1-(2-cyanoethyl)-4-nitroimidazole 在 羟胺 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以72%的产率得到1-(4-nitroimidazole-1-yl)-propanhydroxyiminoamide
  参考文献：
  名称：

  Synthesis and biological results of the technetium-99m-labeled 4-nitroimidazole for imaging tumor hypoxia

  摘要：

  1-(4-Nitroimidazole-1-yl)-propanhydroxyiminoamide (N41PA) was synthesized. The biodistribution of Tc-99m-N41PA in mice bearing S180 tumor demonstrated that the complex showed accumulation in tumor and slow clearance from it. The tumor-to-tissue uptake ratios increase with time. These results suggest that Tc-99m-N41PA would be a marker for imaging tumor hypoxia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.017