1-methyl-2-[(E)-2-(4-methylphenyl)vinyl]-5-nitro-1H-imidazole | 41147-44-8

• 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-methyl-2-[(E)-2-(4-methylphenyl)vinyl]-5-nitro-1H-imidazole
• 英文别名: 1-methyl-2-(4-methyl-styryl)-5-nitro-1H-imidazole；1-methyl-2-[(E)-2-(4-methylphenyl)ethenyl]-5-nitroimidazole
• CAS: 41147-44-8
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: NCZRWIJIOVVGQF-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-methyl-2-[(E)-2-(4-methylphenyl)vinyl]-5-nitro-1H-imidazole 在 吡啶 、 potassium carbonate 、 对甲苯磺酰肼 作用下， 反应 14.0h， 以18%的产率得到1-methyl-2-[2-(4-methylphenyl)ethyl]-5-nitro-1H-imidazole
  参考文献：
  名称：

  Synthesis and Electrochemistry of 2-Ethenyl and 2-Ethanyl Derivatives of 5-Nitroimidazole and Antimicrobial Activity against Giardia lamblia

  摘要：

  Infections with the diarrheagenic pathogen, Giardia lamblia, are commonly treated with the 5-nitroimidazole (5-NI) metronidazole (Mz), and yet treatment failures and Mz resistance occur. Using a panel of new 2-ethenyl and 2-ethanyl 5-NI derivatives, we found that compounds with a saturated bridge between the 5-NI core and a pendant ring system exhibited only modestly increased antigiardial activity and could not overcome Mz resistance. By contrast, olefins with a conjugated bridge connecting the core and a substituted phenyl or heterocyclic ring showed greatly increased antigiardial activity without toxicity, and several overcame Mz resistance and were more effective than Mz in a murine giardiasis model. Determination of the half-wave potential of the initial one-electron transfer by cyclic voltammetry revealed that easier redox activation correlated with greater antigiardial activity and capacity to overcome Mz resistance. These studies show the potential of combining systematic synthetic approaches with biological and electrochemical evaluations in developing improved 5-NI drugs.

  DOI：

  10.1021/jm900356n
• 作为产物：
  描述：

  二甲硝咪唑 、 对甲基苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以22%的产率得到1-methyl-2-[(E)-2-(4-methylphenyl)vinyl]-5-nitro-1H-imidazole
  参考文献：
  名称：

  Synthesis and Electrochemistry of 2-Ethenyl and 2-Ethanyl Derivatives of 5-Nitroimidazole and Antimicrobial Activity against Giardia lamblia

  摘要：

  Infections with the diarrheagenic pathogen, Giardia lamblia, are commonly treated with the 5-nitroimidazole (5-NI) metronidazole (Mz), and yet treatment failures and Mz resistance occur. Using a panel of new 2-ethenyl and 2-ethanyl 5-NI derivatives, we found that compounds with a saturated bridge between the 5-NI core and a pendant ring system exhibited only modestly increased antigiardial activity and could not overcome Mz resistance. By contrast, olefins with a conjugated bridge connecting the core and a substituted phenyl or heterocyclic ring showed greatly increased antigiardial activity without toxicity, and several overcame Mz resistance and were more effective than Mz in a murine giardiasis model. Determination of the half-wave potential of the initial one-electron transfer by cyclic voltammetry revealed that easier redox activation correlated with greater antigiardial activity and capacity to overcome Mz resistance. These studies show the potential of combining systematic synthetic approaches with biological and electrochemical evaluations in developing improved 5-NI drugs.

  DOI：

  10.1021/jm900356n

文献信息

• [EN] EXPANDED THERAPEUTIC POTENTIAL IN NITROHETEROARYL ANTIMICROBIALS<br/>[FR] POTENTIEL THÉRAPEUTIQUE ÉTENDU DANS DES ANTIMICROBIENS À NITROHÉTÉROARYLE
  申请人：UNIV CALIFORNIA

  公开号：WO2014205414A1

  公开（公告）日：2014-12-24

  Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to imidazole, thiazole, and furan derivatives and their use as therapeutic agents.

  本文披露了抗微生物化合物组合物、药物组合物及其使用和制备。一些实施例涉及咪唑、噻唑和呋喃衍生物及其作为治疗剂的用途。
• Synthesis, Spectroscopic and Structural Studies of New 2-Substituted 4- Nitroimidazoles
  作者：Hayette Alliouche、Abdelmalek Bouraiou、Sofiane Bouacida、Mebarek Bahnous、Thierry Roisnel、Ali Belfaitah

  DOI：10.2174/15701786113106660090

  日期：2014.2

  This study describes the synthesis of novel 4-nitro-2-substitutedimidazole derivatives via a transposition reaction of nitro group. Conversion of 5-nitro-2-phenylethanol (styryl) imidazole derivatives into the corresponding 4- nitroisomers was achieved in good yields in nitrobenzene using a catalytic amount of methyl iodide. Spectroscopic study and single crystal X-ray structures are reported for five compounds to understand the conformational structures of these compounds.

  本研究描述了通过硝基的转位反应合成新型 4-硝基-2-取代咪唑衍生物的过程。在碘化甲烷的催化下，5-硝基-2-苯乙醇（苯乙烯基）咪唑衍生物在硝基苯中以良好的收率转化为相应的 4-硝基异构体。报告了五种化合物的光谱研究和单晶 X 射线结构，以了解这些化合物的构象结构。
• EXPANDED THERAPEUTIC POTENTIAL IN NITROHETEROARYL ANTIMICROBIALS
  申请人：The Regents of the University of California

  公开号：US20160244435A1

  公开（公告）日：2016-08-25

  Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to imidazole, thiazole, and furan derivatives and their use as therapeutic agents.

  本文披露了抗微生物化合物组成物、制药组合物、其使用和制备方法。其中一些实施例涉及咪唑、噻唑和呋喃衍生物及其作为治疗剂的使用。