6-nitro-1H-benzimidazole-1-propionamidooxime | 58553-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-nitro-1H-benzimidazole-1-propionamidooxime
• 英文别名: 6-Nitro-1-benzimidazol-propionamidoxin；3-(6-nitro-benzoimidazol-1-yl)-propionamide oxime；N'-hydroxy-3-(6-nitrobenzimidazol-1-yl)propanimidamide
• CAS: 58553-92-7
• 化学式: C₁₀H₁₁N₅O₃
• 分子量: 249.229
• InChiKey: FSMVTWBFSJAXDE-UHFFFAOYSA-N

物化性质

• 沸点：
  492.7±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(6-nitrobenzimidazol-1-yl)propionitrile 在 羟胺 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以41%的产率得到6-nitro-1H-benzimidazole-1-propionamidooxime
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of the 99mTc labeled nitrobenzoimidazole and nitrotriazole as tumor hypoxia markers

  摘要：

  1-(3-1 2,4-Nitrotriazole-1-yl)-propanhydroxyiminoamide and 1-(6-nitrobenzoimidazole-1-yl)-propanhydroxyiminoamide were synthesized and radiolabeled with Tc-99m. The Tc-99m labeled complexes continuously accumulated in hypoxic marine sarcoma S180 cells in vitro but not in aerobic cells. Biodistribution results in mice bearing S180 tumor indicated that the tracers could localize in tumor and eliminate from it slowly. These results suggested that the Tc-99m labeled nitrobenzoimidazole and nitrotriazole might be the novel tumor hypoxia markers. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.001

文献信息

• Antiparasitic agents. 6. Synthesis and anthelmintic activities of novel isothiocyanatophenyl-1,2,4-oxadiazoles
  作者：R. D. Haugwitz、A. J. Martinez、J. Venslavsky、R. G. Angel、B. V. Maurer、G. A. Jacobs、V. L. Narayanan、L. R. Cruthers、J. Szanto

  DOI：10.1021/jm00147a019

  日期：1985.9

  The syntheses and anthelmintic activities of 31 3- and 5-(isothiocyanatophenyl)-1,2,4-oxadiazoles are reported. In the primary anthelmintic screen, 3-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (39) showed 100% nematocidal activity and 3-(2-furanyl)-5-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (63), 3-(2-furanyl)-5-(2-chloro-4-isothiocyanatophenyl)-1,2,4-oxadiazole (64), and 3-(2-furanyl)-5-(4-chloro-3-isothiocyanatophenyl)-1,2,4-oxadiazole (66) showed 100% taeniacidal activity when administered orally to mice. The two most active members of this series, 39 and 63, were active against the gastrointestinal nematodes of sheep at 100 mg/kg. In addition, 39 was also found to be active against hookworms in dogs at a single, oral dose of 200 mg/kg.
• Synthesis and preliminary biological evaluation of the 99mTc labeled nitrobenzoimidazole and nitrotriazole as tumor hypoxia markers
  作者：Yu Zhang、Taiwei Chu、Xuguang Gao、Xinqi Liu、Zhi Yang、Zhenquan Guo、Xiangyun Wang

  DOI：10.1016/j.bmcl.2006.01.001

  日期：2006.4

  1-(3-1 2,4-Nitrotriazole-1-yl)-propanhydroxyiminoamide and 1-(6-nitrobenzoimidazole-1-yl)-propanhydroxyiminoamide were synthesized and radiolabeled with Tc-99m. The Tc-99m labeled complexes continuously accumulated in hypoxic marine sarcoma S180 cells in vitro but not in aerobic cells. Biodistribution results in mice bearing S180 tumor indicated that the tracers could localize in tumor and eliminate from it slowly. These results suggested that the Tc-99m labeled nitrobenzoimidazole and nitrotriazole might be the novel tumor hypoxia markers. (C) 2006 Elsevier Ltd. All rights reserved.