2-(2-methoxy-4-nitro-1H-imidazol-1-yl)-1-phenylethan-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-methoxy-4-nitro-1H-imidazol-1-yl)-1-phenylethan-1-ol
• 英文别名: 2-(2-methoxy-4-nitro-1H-imidazol-1-yl)-1-phenylethanol；2-(2-Methoxy-4-nitro-imidazol-1-yl)-1-phenyl-ethanol；2-(2-methoxy-4-nitroimidazol-1-yl)-1-phenylethanol
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: OYLDHNRPPJURSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (±)-2-氯-1-苯基乙醇 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(2-methoxy-4-nitro-1H-imidazol-1-yl)-1-phenylethan-1-ol
  参考文献：
  名称：

  Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole

  摘要：

  We have designed and synthesized econazole-derived nitroimidazoles to investigate the antitubercular activity of the nitroimidazole compounds. The introduction of a nitro group at the 4-position of the imidazole on econazole abolished the antitubercular activity. However, alcoholic nitroimidazoles 4 and 6 compounds were active against Mycobacterium tuberculosis (Mtb). While the MIC value of econazole was 16 mu g/mL, the MIC of 6a and 6f turned out to be 0.5 mu g/mL. In particular, the activity of 6f against non-replicating Mtb was as good as PA-824, which is currently in clinical phase II studies as an antitubercular agent. Overall, alcohol compounds 4 and 6 tend to be more active than ether compounds 5 and 7. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.128

文献信息

• Additive-free oxychlorination of unsaturated C–C bonds with <i>tert</i>-butyl hypochlorite and water
  作者：Duyi Shen、Chaoyue Sun、Yun Han、Zhen Luo、Ting Ren、Qin Zhang、Wenting Huang、Jianru Xie、Ying Jia、Mianran Chao

  DOI：10.1039/d4ob00003j

  日期：2024.4.17

  α-dichloroketones and α-chlorohydrins from various aryl terminal, diaryl internal, and aliphatic terminal alkynes and alkenes, respectively. The commercially available tert-butyl hypochlorite (tBuOCl) was employed as a suitable chlorinating reagent, being accompanied by the less harmful tBuOH as the by-product. In addition, the oxygen atoms in the products came from water rather than molecular oxygen, based on

  在此，我们报告了一种无添加剂的方案，用于分别从各种芳基末端、二芳基内部和脂肪族末端炔烃和烯烃轻松合成α,α-二氯酮和α-氯醇。使用市售的次氯酸叔丁酯（ t BuOCl）作为合适的氯化剂，并伴随副产物危害较小的t BuOH。此外，根据18 个O 标记实验，产品中的氧原子来自水而不是分子氧。同时，对Z-烯烃和相应的E-烯烃的非对映选择性进行了比较和合理化。通过一组对照实验，提出了可能的机制，即通常以马尔可夫尼科夫加成方式对不饱和 C-C 键进行初始亲电氯化，然后与水进行亲核加成。这项工作简化了在环境条件下使用温和氯源和绿色氧源的氧氯化方法。
• Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole
  作者：Sang-Ho Lee、Suhyun Kim、Min-Han Yun、Yong Sup Lee、Sang-Nae Cho、Taegwon Oh、Pilho Kim

  DOI：10.1016/j.bmcl.2010.12.128

  日期：2011.3

  We have designed and synthesized econazole-derived nitroimidazoles to investigate the antitubercular activity of the nitroimidazole compounds. The introduction of a nitro group at the 4-position of the imidazole on econazole abolished the antitubercular activity. However, alcoholic nitroimidazoles 4 and 6 compounds were active against Mycobacterium tuberculosis (Mtb). While the MIC value of econazole was 16 mu g/mL, the MIC of 6a and 6f turned out to be 0.5 mu g/mL. In particular, the activity of 6f against non-replicating Mtb was as good as PA-824, which is currently in clinical phase II studies as an antitubercular agent. Overall, alcohol compounds 4 and 6 tend to be more active than ether compounds 5 and 7. (C) 2010 Elsevier Ltd. All rights reserved.