1-(2-溴乙基)-2-硝基-1H-咪唑 | 115398-62-4

• 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
• 中文名称: 1-(2-溴乙基)-2-硝基-1H-咪唑
• 英文名称: 1-(2-bromoethyl)-2-nitro-1H-imidazole
• 英文别名: 1-(2'-Bromoethyl)-2-nitroimidazole；1-(2-bromoethyl)-2-nitroimidazole
• CAS: 115398-62-4
• 化学式: C₅H₆BrN₃O₂
• 分子量: 220.026
• InChiKey: QAUAYTPRIZLIPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-溴乙基)-2-硝基-1H-咪唑 生成 N-[1-(2-bromoethyl)imidazol-2-yl]hydroxylamine
  参考文献：
  名称：

  2-(羟基氨基)咪唑在水溶液中分解的动力学和机理

  摘要：

  Les hydroxyamino-2 imidazoles sont convertis en ions (amino-2 dihydro-4,5 dihydroxy-4,5) imidazoliums

  DOI：

  10.1021/ja00203a018
• 作为产物：
  描述：

  2-硝基咪唑 、 1,2-二溴乙烷 在 氢氧化钾 、 18-冠醚-6 作用下， 以57%的产率得到1-(2-溴乙基)-2-硝基-1H-咪唑
  参考文献：
  名称：

  An Efficient Procedure for the 1-Alkylation of 2-Nitroimidazoles and the Synthesis of a Probe for Hypoxia in Solid Tumours

  摘要：

  裸露阴离子形式的2-硝基咪唑的N-烷基化反应，通过其在冠醚存在下由碱金属盐形成的均相溶液中进行，已被证明是一种有用的制备方法。α,ω-二卤代烷的反应可以被调控，以获得单或双杂芳基烷。该方法已被用于碱基化茶碱，并制备了一种可作为探针的化合物，用于在固体肿瘤组织切片中鉴定、定位和量化缺氧区域。

  DOI：

  10.1055/s-1991-26552

文献信息

• Synthesis of nitroimidazole derived oxazolidinones as antibacterial agents
  作者：Vandana Varshney、Nripendra N. Mishra、Praveen K. Shukla、Devi P. Sahu

  DOI：10.1016/j.ejmech.2009.11.009

  日期：2010.2

  A series of N-alkylated derivatives of nitroimidazolyl oxazolidinones 6a–i with various substituent at N-1 position of the nitroimidazole were synthesized and their in-vitro antibacterial activities were evaluated against several Gram-positive and Gram-negative bacteria. The 6a was found to be most potent compound in the series with MIC at 0.097 μg/mL against Bacillus cereus MTCC 430.). Both 6a and

  合成了一系列在硝基咪唑的N-1位具有多个取代基的硝基咪唑基恶唑烷酮6a - i的N烷基化衍生物，并评估了它们对几种革兰氏阳性和革兰氏阴性细菌的体外抗菌活性。在图6a是在0.097微克/毫升发现在该系列中具有MIC最有效的化合物对蜡状芽孢杆菌MTCC 430）。两个图6A和6F没有向哺乳动物细胞L929表现出任何毒性。
• Design, synthesis and biological evaluation of 6-(nitroimidazole-1H-alkyloxyl)-4-anilinoquinazolines as efficient EGFR inhibitors exerting cytotoxic effects both under normoxia and hypoxia
  作者：Weiyan Cheng、Shijun Zhu、Xiaodong Ma、Ni Qiu、Peng Peng、Rong Sheng、Yongzhou Hu

  DOI：10.1016/j.ejmech.2014.11.010

  日期：2015.1

  A series of novel 6-(nitroimidazole-1H-alkyloxyl)-4-anilinoquinazoline derivatives (15a–15r) were designed, synthesized and evaluated as efficient EGFR inhibitors through introduction of hypoxia activated nitroimidazole moiety into the quinazoline scaffold of EGFR inhibitors. The majority of these newly synthesized compounds exhibited comparable EGFR inhibitory activities to gefitinib and moderate

  通过将低氧活化的硝基咪唑基团引入EGFR抑制剂的喹唑啉骨架中，设计，合成和评估了一系列新型的6-（硝基咪唑-1 H-烷氧基）-4-苯胺基喹唑啉衍生物（15a – 15r），并将其评估为有效的EGFR抑制剂。这些新合成的化合物中的大多数在常氧和低氧条件下对吉非替尼表现出可比的EGFR抑制活性，对HT-29细胞具有中等至优异的抗增殖活性。最有前途的化合物15c中所显示的IC 50 0.47 nM的针对EGFR的激酶值和优异的细胞毒性作用对HT-29细胞在含氧量正常和低氧与IC 50值分别为2.21μM和1.62μM。模拟还原激活研究表明，化合物15c在缺氧条件下具有还原激活特性，这与体外代谢研究一致，在体外代谢研究中，15c在缺氧条件下易于还原激活，在常氧条件下稳定性更高。所有这些结果表明15c在常氧和低氧下都是潜在的癌症治疗剂，值得进一步开发。
• Syntheses of 2-Nitroimidazole Derivatives Conjugated with 1,4,7-Triazacyclononane-<i>N</i>,<i>N</i>′-Diacetic Acid Labeled with F-18 Using an Aluminum Complex Method for Hypoxia Imaging
  作者：Lathika Hoigebazar、Jae Min Jeong、Ji-Youn Lee、Dinesh Shetty、Bo Yeun Yang、Yun-Sang Lee、Dong Soo Lee、June-Key Chung、Myung Chul Lee

  DOI：10.1021/jm201611a

  日期：2012.4.12

  Hypoxia imaging is important for diagnosis of ischemic diseases, and thus various F-18-labeled radiopharmaceuticals have been developed. However, F-18-labeling requires multistep procedures including azeotropic distillation, which is complicated and difficult to automate. Recently, F-18-labeling method using Al-F complex in aqueous solution was devised that offered a straightforward F-18-labeling procedure. We synthesized nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane-1,4-diacetic acid (NODA) that can be labeled with F-18 using Al-F complex and examined their radiochemistries, in vitro and in vivo biological properties, and animal PET imaging characteristics. We found that the synthesized derivatives have excellent F-18-labeling efficiencies, high stabilities, specific uptakes in cultured hypoxic tumor cells, and high tumor to nontumor ratios in xenografted mice. Furthermore, the derivatives were labeled with F-18 in a straightforward manner within 15 min at high labeling efficiencies and radiochemical purities. In conclusion, F-18-labeled NODA-nitroimidazole conjugates were developed and proved to be promising hypoxia PET agents.
• An Efficient Procedure for the 1-Alkylation of 2-Nitroimidazoles and the Synthesis of a Probe for Hypoxia in Solid Tumours
  作者：Anthony Long、John Parrick、Richard J. Hodgkiss

  DOI：10.1055/s-1991-26552

  日期：——

  The N-alkylation of 2-nitroimidazole through its 'naked' anion, formed from its alkali metal salts in the presence of crown ethers and in homogeneous solution, is shown to be a useful preparative procedure. The reactions of α,ω-dihaloalkanes can be controlled to afford either the mono- or diheteroarylalkane. The procedure has been used to alkylate theophylline and to prepare a compound of use as a probe to identify, locate and quantify hypoxia in sections from solid tumours.

  裸露阴离子形式的2-硝基咪唑的N-烷基化反应，通过其在冠醚存在下由碱金属盐形成的均相溶液中进行，已被证明是一种有用的制备方法。α,ω-二卤代烷的反应可以被调控，以获得单或双杂芳基烷。该方法已被用于碱基化茶碱，并制备了一种可作为探针的化合物，用于在固体肿瘤组织切片中鉴定、定位和量化缺氧区域。
• Kinetics and mechanism of the decomposition in aqueous solutions of 2-(hydroxyamino)imidazoles
  作者：Judy L. Bolton、Robert A. McClelland

  DOI：10.1021/ja00203a018

  日期：1989.10

  Les hydroxyamino-2 imidazoles sont convertis en ions (amino-2 dihydro-4,5 dihydroxy-4,5) imidazoliums

  Les hydroxyamino-2 imidazoles sont convertis en ions (amino-2 dihydro-4,5 dihydroxy-4,5) imidazoliums