1-(3-hydroxypropyl)-4-nitroimidazole | 13230-17-6

• 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-(3-hydroxypropyl)-4-nitroimidazole
• 英文别名: 3-(4-nitro-1H-imidazol-1-yl)propan-1-ol；1-(γ-Hydroxypropyl)-4-nitroimidazol；3-(4-nitro-imidazol-1-yl)-propan-1-ol；3-(4-nitroimidazol-1-yl)propan-1-ol
• CAS: 13230-17-6
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: RRYKREHVYKJWEU-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  434.2±25.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxypropyl)-4-nitroimidazole 、 青蒿琥酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以62%的产率得到
  参考文献：
  名称：

  Artemisinin-indole and artemisinin-imidazole hybrids: Synthesis, cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells

  摘要：

  A series of artemisinin derivatives with MDR reversal activity were designed and synthesized. All hybrids were screened to anticancer activities against four human cancer cell lines (A549, MCF-7, HepG-2, MDA-MB-231) and normal human hepatic cell (L02) in vitro. Most of the new compounds showed higher anticancer activities than artemisinin, among which compounds 11a and 11c displayed superior potency with IC50 6.78 mu M and 5.25 mu M against MCF-7, respectively. The further research indicated that the most potent 11c induced cell cycle arrest at G2 phase in MCF-7. Additionally, compound 11c showed remarkable MDR reversal activity which reversed adriamycin against MCF-7/ADR cells with IC50 0.76 mu M.

  DOI：

  10.1016/j.bmcl.2019.02.021
• 作为产物：
  描述：

  1-(3-bromopropyl)-4-nitroimidazole 在 水 、 potassium carbonate 作用下， 反应 0.67h， 以97%的产率得到1-(3-hydroxypropyl)-4-nitroimidazole
  参考文献：
  名称：

  氨基聚苯乙烯负载的六甘醇桥接离子液体作为水介导的亲核羟基化的高效非均相催化剂†

  摘要：

  我们报告了一种基于氨基苯乙烯与带有六甘醇部分的 1-乙烯基咪唑离子液体的共聚制备氨基聚苯乙烯负载的六甘醇桥接离子液体 (APS-HEGBIL) 的简单且环保的方法及其表征通过几种分析技术。发现所得的 APS-HEGBIL 催化剂在催化卤代烷的选择性亲核羟基化以在水中产生相应的醇方面非常有效，该醇充当溶剂和亲核氢氧化物源。该催化剂在十次循环后易于回收并保持其催化活性和稳定性，并具有优异的收率。该催化剂的主要特性是它在反应过程中显着提高了水的亲核性，并促进了极性和碱敏感的卤代烷反应物以优异的收率快速转化为醇。离子液体和聚合物材料的结合提供了准均相催化剂，这些催化剂通过简单的过滤回收，并为进行催化过程提供了环境友好的手段。

  DOI：

  10.1039/c9ra00590k

文献信息

• Nucleophilic Hydroxylation in Water Media Promoted by a Hexa-Ethylene Glycol-Bridged Dicationic Ionic Liquid
  作者：Vinod H. Jadhav、Jin Gwan Kim、Hyeon Jin Jeong、Dong Wook Kim

  DOI：10.1021/acs.joc.5b00901

  日期：2015.7.17

  Hexaethylene glycol bis(3-hexaethylene glycol imidazolium) dimesylate ionic liquid (hexaEG-DHIM) was designed and prepared as a highly efficient promoter for the nucleophilic hydroxylation of alkyl halides to the corresponding alcohol products in neat water media. It was observed that hexaEG-DHIM promoter enhanced the nucleophilicity of water significantly in the reaction. In addition, the hexaEG-DHIM could be reused several times without loss of activity. Moreover, the hydroxylation reactions of base-sensitive and/or polar alkyl halide substrates proceeded highly chemoselectively in excellent yields.
• Amino-polystyrene supported hexaethylene glycol-bridged ionic liquid as an efficient heterogeneous catalyst for water-mediated nucleophilic hydroxylation
  作者：Mudumala Veeranarayana Reddy、Seok Min Kang、Suah Yoo、Sang Sik Woo、Dong Wook Kim

  DOI：10.1039/c9ra00590k

  日期：——

  amino-polystyrene supported hexaethylene glycol-bridged ionic liquid (APS-HEGBIL) based on the copolymerization of amino-styrene with 1-vinyl imidazolium ionic liquid bearing hexaethylene glycol moieties, and its characterization by several analytical techniques. The resulting APS-HEGBIL catalyst was found to be remarkably efficient at catalyzing the selective nucleophilic hydroxylation of alkyl halides to produce

  我们报告了一种基于氨基苯乙烯与带有六甘醇部分的 1-乙烯基咪唑离子液体的共聚制备氨基聚苯乙烯负载的六甘醇桥接离子液体 (APS-HEGBIL) 的简单且环保的方法及其表征通过几种分析技术。发现所得的 APS-HEGBIL 催化剂在催化卤代烷的选择性亲核羟基化以在水中产生相应的醇方面非常有效，该醇充当溶剂和亲核氢氧化物源。该催化剂在十次循环后易于回收并保持其催化活性和稳定性，并具有优异的收率。该催化剂的主要特性是它在反应过程中显着提高了水的亲核性，并促进了极性和碱敏感的卤代烷反应物以优异的收率快速转化为醇。离子液体和聚合物材料的结合提供了准均相催化剂，这些催化剂通过简单的过滤回收，并为进行催化过程提供了环境友好的手段。
• Artemisinin-indole and artemisinin-imidazole hybrids: Synthesis, cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells
  作者：Yanping Hu、Na Li、Jiayao Zhang、Ying Wang、Li Chen、Jianbo Sun

  DOI：10.1016/j.bmcl.2019.02.021

  日期：2019.5

  A series of artemisinin derivatives with MDR reversal activity were designed and synthesized. All hybrids were screened to anticancer activities against four human cancer cell lines (A549, MCF-7, HepG-2, MDA-MB-231) and normal human hepatic cell (L02) in vitro. Most of the new compounds showed higher anticancer activities than artemisinin, among which compounds 11a and 11c displayed superior potency with IC50 6.78 mu M and 5.25 mu M against MCF-7, respectively. The further research indicated that the most potent 11c induced cell cycle arrest at G2 phase in MCF-7. Additionally, compound 11c showed remarkable MDR reversal activity which reversed adriamycin against MCF-7/ADR cells with IC50 0.76 mu M.