2-ethyl-1-(5-fluoro-2-nitrophenyl)-4-methyl-1H-imidazole | 133307-22-9

• 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-ethyl-1-(5-fluoro-2-nitrophenyl)-4-methyl-1H-imidazole
• 英文别名: 2-(2-ethyl-4-methyl-imidazol-1-yl)-4-fluoro-nitrobenzene；2-Ethyl-1-(2-nitro-5-fluorophenyl)-4-methyl-1H-imidazole；2-ethyl-1-(5-fluoro-2-nitrophenyl)-4-methylimidazole
• CAS: 133307-22-9
• 化学式: C₁₂H₁₂FN₃O₂
• 分子量: 249.245
• InChiKey: DXIRNCUUPYGCQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethyl-1-(5-fluoro-2-nitrophenyl)-4-methyl-1H-imidazole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 2.0h， 生成 2-(2-Ethyl-4-methyl-imidazol-1-yl)-4-imidazol-1-yl-phenylamine
  参考文献：
  名称：

  Novel compounds possessing potent cAMP and cGMP phosphodiesterase inhibitory activity. Synthesis and cardiovascular effects of a series of imidazo[1,2-a]quinoxalinones and imidazo[1,5-a]quinoxalinones and their aza analogs

  摘要：

  A series of novel imidazoquinoxalinones and their aza analogues were prepared by the cyclization of o-amino(H-1-imidazol-1-yl)aryls and heteroaryls with carbonyldiimidazole. The compounds were screened for inhibition of Type I and Type IV phosphodiesterases (PDE's) and evaluated for their vasorelaxant and positive inotropic activities in vitro. In general, compounds having potent PDE inhibitory activity also possessed good inotropic and vasodilator activity, although linear correlations between these activities could not be established.

  DOI：

  10.1021/jm00113a002
• 作为产物：
  描述：

  2,4-二氟硝基苯 、 2-乙基-4-甲基咪唑 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以63%的产率得到2-ethyl-1-(5-fluoro-2-nitrophenyl)-4-methyl-1H-imidazole
  参考文献：
  名称：

  Novel compounds possessing potent cAMP and cGMP phosphodiesterase inhibitory activity. Synthesis and cardiovascular effects of a series of imidazo[1,2-a]quinoxalinones and imidazo[1,5-a]quinoxalinones and their aza analogs

  摘要：

  A series of novel imidazoquinoxalinones and their aza analogues were prepared by the cyclization of o-amino(H-1-imidazol-1-yl)aryls and heteroaryls with carbonyldiimidazole. The compounds were screened for inhibition of Type I and Type IV phosphodiesterases (PDE's) and evaluated for their vasorelaxant and positive inotropic activities in vitro. In general, compounds having potent PDE inhibitory activity also possessed good inotropic and vasodilator activity, although linear correlations between these activities could not be established.

  DOI：

  10.1021/jm00113a002

文献信息

• ARYL AND HETEROARYL FUSED IMIDAZO[1,5-a]PYRAZINES AS INHIBITORS OF PHOSPHODIESTERASE 10
  申请人：Malamas Michael S.

  公开号：US20090143367A1

  公开（公告）日：2009-06-04

  The invention relates to imidazo[1,5-a]pyrazine derivatives, to processes for preparing them, to pharmaceutical preparations which comprise these compounds and to the pharmaceutical use of these compounds, which are inhibitors of phosphodiesterase 10 (PDE10), as active compounds for treating central nervous system diseases of mammals, including humans.

  这项发明涉及咪唑并[1,5-a]吡嗪衍生物，涉及制备它们的方法，包括这些化合物的药物制剂以及将这些化合物作为磷酸二酯酶10（PDE10）的抑制剂作为活性成分，用于治疗哺乳动物，包括人类的中枢神经系统疾病的药物用途。
• Aryl and heteroaryl fused imidazo [1,5-a] pyrazines as inhibitors of phosphodiesterase 10
  申请人：Hofgen Norbert

  公开号：US20090143391A1

  公开（公告）日：2009-06-04

  The invention relates to imidazo[1,5-a]pyrazine derivatives, to processes for preparing them, to pharmaceutical preparations which comprise these compounds and to the pharmaceutical use of these compounds, which are inhibitors of phosphodiesterase 10 (PDE10), as active compounds for treating central nervous system diseases of mammals, including humans.

  该发明涉及咪唑并[1,5-a]吡嗪衍生物，涉及制备它们的方法，包括这些化合物的药物制剂以及这些化合物的药用，这些化合物是磷酸二酯酶10（PDE10）的抑制剂，作为治疗哺乳动物中枢神经系统疾病的活性化合物，包括人类。
• Process for the preparation of imidazoquinoxalinones
  申请人：Berlex Laboratories, Inc.

  公开号：US05166344A1

  公开（公告）日：1992-11-24

  This invention relates to novel imidazoquinoxalinones and their aza analogs and to a process for their preparation. The compounds of this invention have been found to have inodilatory, vasodilatory, venodilatory and other pharmacologic effects.

  本发明涉及新型咪唑喹喔啉酮及其氮杂环类似物，以及它们的制备方法。本发明的化合物已被发现具有内皮舒张、血管扩张、静脉扩张和其他药理作用。
• Imidazoquinoxalinones, their aza analogs and process for their
  申请人：Berlex Laboratories, Inc.

  公开号：US05055465A1

  公开（公告）日：1991-10-08

  This invention relates to novel imidazoquinoxalinones and their aza analogs and to a process for their preparation. The compounds of this invention have been found to have inodilatory, vasodilatory, venodilatory and other pharmacologic effects.

  本发明涉及新型咪唑喹喔啉酮及其氮杂环衍生物以及它们的制备方法。本发明的化合物被发现具有无嗅性、血管扩张、静脉扩张和其他药理作用。
• Imidazoquinoxalinones, their aza analogs and process for their preparation
  申请人：BERLEX LABORATORIES, INC.

  公开号：EP0400583A1

  公开（公告）日：1990-12-05

  This invention relates to novel imidazoquinoxalinones and their aza analogs and to a process for their preparation. The compounds of this invention have been found to have inodilatory, vasodilatory, venodilatory and other pharmacologic effects.

  本发明涉及新型咪唑喹喔啉酮及其氮杂类似物，以及其制备工艺。已发现本发明的化合物具有扩张血管、扩张静脉和其他药理作用。