2-[(E)-2-(3-methoxyphenyl)vinyl]-1-methyl-5-nitro-1H-imidazole | 1161926-06-2

• 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-[(E)-2-(3-methoxyphenyl)vinyl]-1-methyl-5-nitro-1H-imidazole
• 英文别名: 2-[(E)-2-(3-methoxyphenyl)ethenyl]-1-methyl-5-nitroimidazole
• CAS: 1161926-06-2
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: AHFRJJJSASSBCT-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二甲硝咪唑 、 3-甲氧基苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以32%的产率得到2-[(E)-2-(3-methoxyphenyl)vinyl]-1-methyl-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。
• 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。
• PHENYLETHENYL OR PHENYLETHINYL DERIVATIVES AS GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1349839B1

  公开（公告）日：2005-02-09
• Synthesis and Electrochemistry of 2-Ethenyl and 2-Ethanyl Derivatives of 5-Nitroimidazole and Antimicrobial Activity against <i>Giardia lamblia</i>
  作者：Carlos A. Valdez、Jonathan C. Tripp、Yukiko Miyamoto、Jaroslaw Kalisiak、Petr Hruz、Yolanda S. Andersen、Sabrina E. Brown、Karina Kangas、Leo V. Arzu、Barbara J. Davids、Frances D. Gillin、Jacqueline A. Upcroft、Peter Upcroft、Valery V. Fokin、Diane K. Smith、K. Barry Sharpless、Lars Eckmann

  DOI：10.1021/jm900356n

  日期：2009.7.9

  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.