2-硝基-5-甲基-1H-咪唑-1-乙醇 | 23571-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-硝基-5-甲基-1H-咪唑-1-乙醇
• 英文名称: 5-methyl-2-nitro-imidazole-1-ethanol
• 英文别名: 2-(5-methyl-2-nitro-imidazol-1-yl)-ethanol；1-(2-Hydroxyethyl)-5-methyl-2-nitroimidazol；5-Methyl-2-nitroimidazole-1-ethanol；2-(5-methyl-2-nitroimidazol-1-yl)ethanol
• CAS: 23571-38-2
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: FIIUIEQMEKWLPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 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

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-硝基-5-甲基-1H-咪唑-1-乙醇 以61%的产率得到
  参考文献：
  名称：

  CAVALLERI B.; VOLPE G.; ARIOLI V., J. MED. CHEM. , 1977, 20, NO 5, 656-660

  摘要：

  DOI：

文献信息

• [EN] NOVEL AMINOPYRIDINES AND THEIR USE IN TREATING CANCER<br/>[FR] NOUVELLES AMINOPYRIDINES ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2022064430A1

  公开（公告）日：2022-03-31

  The invention relates to substituted imidazo[4,5-c]pyridine-2-one compounds of Formula (I) and prodrugs of said compounds. Compounds of Formula (I) selectively inhibit the activity of DNA-dependent protein kinase (DNA-PK) and are therefore useful in the treatment of diseases in which inhibition of DNA-PK is beneficial.

  这项发明涉及Formula (I)的取代咪唑并[4,5-c]吡啶-2-酮化合物以及这些化合物的前药。Formula (I)的化合物选择性地抑制DNA-依赖性蛋白激酶(DNA-PK)的活性，因此在治疗需要抑制DNA-PK的疾病中具有用处。
• Synthesis, Characterization and Antimicrobial Activity of Three Gallates Containing Imidazole, Benzimidazole and Triclosan Units
  作者：Zhiyuan Wang、Haibin Gu、Wuyong Chen

  DOI：10.14233/ajchem.2014.15600

  日期：——

  Three new gallates containing the antimicrobial units of imidazole, benzimidazole and triclosan, respectively, were designed and synthesized. Firstly, the direct esterification method, in which p-toluenesulfonic acid was used as the catalyst, was adopted to synthesize the three gallates. Results show that it is infeasible to obtain the target products, especially for the direct esterification reaction of 5-methyl-2-nitro-imidazole-1-ethanol and gallic acid, the synthesized product is just a complex composed by equimolar 5-methyl-2-nitro-imidazole-1-ethanol and gallic acid and stabilized by a lot of intramolecular and intermolecular hydrogen bonds, which was proved by the single-crystal X-ray diffraction analysis. Another, the indirect esterification method, in which the phenolic hydroxyl groups of gallic acid were first protected by acetyls as shown in Scheme-I, was employed. The obtained compounds were proved to be the expected products by elemental analysis, IR, 1H NMR, 13C NMR and X-ray single-crystal diffraction. Finally, the inhibition zone method was used to determine the antimicrobial effect of the synthesized gallates and their initial compounds. Results indicate that the introduction of the three antimicrobial units has obvious synergistic or additive effect on the antimicrobial activities of gallates. The gallates shows different inhibitory effect against different tested microbes, which is mainly decided by the introduced antimicrobial units.

  设计并合成了三种分别含有咪唑、苯并咪唑和三氯生抗菌单元的新型没食子酸盐。首先，以对甲苯磺酸为催化剂，采用直接酯化法合成这三种没食子酸盐。结果表明，直接酯化法无法得到目标产物，尤其是 5-甲基-2-硝基咪唑-1-乙醇与没食子酸的直接酯化反应，合成产物只是由等摩尔的 5-甲基-2-硝基咪唑-1-乙醇和没食子酸组成的复合物，并通过大量分子内和分子间氢键稳定，这一点已被单晶 X 射线衍射分析所证实。另一种是间接酯化法，如方案 I 所示，首先用乙酰基保护没食子酸的酚羟基。通过元素分析、红外光谱、1H NMR、13C NMR 和 X 射线单晶衍射，证明所得到的化合物为预期产物。最后，采用抑菌区法测定了合成的没食子酸盐及其初始化合物的抗菌效果。结果表明，三种抗菌单元的引入对没食子酸盐的抗菌活性具有明显的协同或相加作用。没食子酸盐对不同的受试微生物有不同的抑制作用，这主要是由引入的抗菌单元决定的。
• CAVALLERI B.; VOLPE G.; ARIOLI V., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 5, 656-660
  作者：CAVALLERI B.、 VOLPE G.、 ARIOLI V.

  DOI：——

  日期：——