1-(4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)ethanone | 1609633-21-7

• 英文名称: 1-(4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)ethanone
• CAS: 1609633-21-7
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: XZCCIEOIRYDAAM-UHFFFAOYSA-N

物化性质

• 沸点：
  532.0±35.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.26
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)ethanone 、 2,5-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以81%的产率得到3-(2,5-dimethoxyphenyl)-1-{4-[2-(2-methyl-5-nitro-imidazol-1-yl)ethoxy]phenyl}propenone
  参考文献：
  名称：

  Novel metronidazole–chalcone conjugates with potential to counter drug resistance in Trichomonas vaginalis

  摘要：

  Trichomoniasis is the most prevalent, curable sexually transmitted disease (STD), which increases risk of viral STDs and HIV. However, drug resistance has been developed by some strains of Trichomonas vaginalis against Metronidazole (MTZ), the FDA approved drug against trichomoniasis. In the present study twenty two chalcone hybrids of metronidazole have been synthesized in a quest to get new molecules with higher potential against metronidazole-resistant T vaginalis. All new hybrid molecules were found active against T vaginalis with varying levels of activity against MTZ-susceptible and resistant strains. Eight compounds (4a, 4c, 4d, 4e, 4f, 4h, 4q and 4s) were found as active as the standard drug with an MIC of 1.56 mu g/m1 against MTZ-susceptible strain. However, compounds 4e, 4h and 4m were 4-times more active than MTZ against drug-resistant T vaginalis, amongst which 4e and 4h were most promising against both susceptible and resistant strains. (C) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.03.076
• 作为产物：
  描述：

  甲硝唑 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 1-(4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)ethanone
  参考文献：
  名称：

  Synthesis, Biological Evaluation, Structure–Activity Relationship, and Mechanism of Action Studies of Quinoline–Metronidazole Derivatives Against Experimental Visceral Leishmaniasis

  摘要：

  In our efforts to identify novel chemical scaffolds for the development of antileishmanial agents, a series of quinoline metronidazole hybrid compounds was synthesized and tested against the murine model of visceral leishmaniasis. Among all synthesized derivatives, 15b and 15i showed significant antileishmanial efficacy against both extracellular promastigote (IC50 9.54 and 5.42 mu M, respectively) and intracellular amastigote (IC50 9.81 and 3.75 mu M, respectively) forms of Leishmania donovani with negligible cytotoxicity toward the host 0774 macrophages, Vero cells). However, compound 15i effectively inhibited the parasite burden in the liver and spleen (>80%) of infected BALB/c mice. Mechanistic studies revealed that 15i triggers oxidative stress which induces bioenergetic collapse and apoptosis of the parasite by decreasing ATP production and mitochondrial membrane potential. Structure activity analyses and pharmacokinetic studies suggest 15i as a promising antileishmanial lead and emphasize the importance of quinoline metronidazole series as a suitable platform for the future development of antileishmanial agents.

  DOI：

  10.1021/acs.jmedchem.9b00628