6,7-二氢-2-(4-甲氧基苯基)-3-(4-吡啶基)-5H-吡咯并[1,2-a]咪唑 | 111908-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6,7-二氢-2-(4-甲氧基苯基)-3-(4-吡啶基)-5H-吡咯并[1,2-a]咪唑
• 英文名称: 2-(4-methoxyphenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo [1,2-a]imidazole
• 英文别名: 2-(4-Methoxyphenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole；2-(4-methoxyphenyl)-3-(4-pyridyl)-6,7-dihydro [5H]pyrrolo [1,2-a]imidazole；2-(4-Methoxyphenyl)-3-(4-pyridyl)-6,7-dihydro-(5H)-pyrrolo(1,2-a)imidazole；2-(4-methoxyphenyl)-3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• CAS: 111908-95-3
• 化学式: C₁₈H₁₇N₃O
• 分子量: 291.352
• InChiKey: UIJWMSUSZQORDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  157.5-158.5 °C
• 沸点：
  489.7±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-二氢-2-(4-甲氧基苯基)-3-(4-吡啶基)-5H-吡咯并[1,2-a]咪唑 在 chromium(VI) oxide 、 三乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.0h， 生成 5,6-dihydro-7,7-difluoro-2-(4-Methoxyphenyl)-3-(4-pyridyl)-[7H]-pyrrolo-[1,2-a]-imidazole
  参考文献：
  名称：

  C-7 functionalization of 6,7-dihydro[5H]pyrrolo[1,2-a]imidazoles: Activation via quaternization with MEMCl

  摘要：

  DOI：

  10.1016/s0040-4039(00)70628-9
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 在 potassium tert-butylate 、 氧气 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 6,7-二氢-2-(4-甲氧基苯基)-3-(4-吡啶基)-5H-吡咯并[1,2-a]咪唑
  参考文献：
  名称：

  Regulation of stress-induced cytokine production by pyridinylimidazoles; inhibition of CSBP kinase

  摘要：

  Members of three classes of pyridinylimidazoles bind with varying affinities to CSBP (p38) kinase which is a member of a stress-induced signal transduction pathway. Based upon SAR and protein homology modeling, the pharmacophore and three potential modes of binding to the enzyme are presented. For a subset of pyridinylimidazoles, binding is shown to correlate with inhibition of CSBP kinase activity, whereas no significant inhibition of PKA, PKC alpha and ERK kinase activity is observed. Copyright (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00212-x

文献信息

• Pyrrolo [1,2-a] imidazole and imidazo [1,2a] pyridine derivatives and
  申请人：SmithKline Beecham Corp.

  公开号：US05145858A1

  公开（公告）日：1992-09-08

  Compounds comprising pyridyl and phenyl substituted pyrrolo[1,2-a]imidazole derivatives and pyridyl and phenyl substituted imidazo[1,2-a]pyridine derivatives, pharmaceutical compositions containing said compounds, and their use as 5-lipoxygenase pathway inhibitors.

  包含吡啶基和苯基取代的吡咯[1,2-a]咪唑衍生物和吡啶基和苯基取代的咪唑[1,2-a]吡啶衍生物的化合物，含有该化合物的药物组合物，以及它们作为5-脂氧合酶途径抑制剂的用途。
• Pyrrolo(1,2-a)imidazole and imidazo(1,2-a)pyridine derivatives and their
  申请人：SmithKline Beecham Corporation

  公开号：US05002941A1

  公开（公告）日：1991-03-26

  Compounds comprising pyridyl and phenyl substituted pyrrolo[1,2-a]imidazole derivatives and pyridyl and phenyl substituted imidazo[1,2-a]pyridine derivatives, pharmaceutical compositions containing said compounds, and their use as 5-lipoxygenase pathway inhibitors.

  该专利涉及含有吡啶基和苯基取代的吡咯[1,2-a]咪唑衍生物和吡啶基和苯基取代的咪唑[1,2-a]吡啶衍生物的化合物，含有上述化合物的制药组合物以及它们作为5-脂氧合酶途径抑制剂的用途。
• Pyrrolo[1,2-a]imidazole and imidazo[1,2-a]pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0364204A1

  公开（公告）日：1990-04-18

  Compounds of formula (I) in which one of R or R1 must be alkylsubstituted pyridyl, processes for their preparation, compositions containing them and their use as inhibitors of 5-lipoxygenase.

  式 (I) 的化合物 其中 R 或 R1 之一必须是烷基取代的吡啶基、其制备工艺、含有它们的组合物以及它们作为 5-脂氧合酶抑制剂的用途。
• Monokine activity interference
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0403251A2

  公开（公告）日：1990-12-19

  A method of treating a human afflicted with a T Cell Viral (TIV) infection, such as a human immunodeflciency virus (HIV) infection ,which comprises administering to such human an effective, monokine activity interfering amount of a monokine activity interfering agent.

  一种治疗 T 细胞病毒（TIV）感染（如人类免疫缺陷病毒（HIV）感染）患者的方法，包括向患者施用有效的、可干扰单核因子活性的单核因子活性干扰剂。
• Medicament for the inhibition of interleukin-1 or tumor necrosis factor production by monocytes and/or macrophages
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0411754A2

  公开（公告）日：1991-02-06

  A method of inhibiting the production of interleukin-1 by monocytes and/or macrophages in a human in need thereof which comprises administering to such a human an effective, interleukin-1 production inhibiting amount of a diaryl-substituted imidazole fused to a second heterocyclic ring containing a nitrogen bridgehead atom wherein said second ring may also contain sulfur, oxygen or an additional nitrogen atom, and may contain additional unsaturation. This invention relates to a method of inhibiting the production of Tumor Necrosis Factor (TNF) by monocytes or macrophages in a human in need thereof which comprises administering to such mammal an effective, TNF production inhibiting amount of a compound of Formula (I) as described herein. The compounds of Formula (II) are generally described as diaryl-substituted imidazole fused to a second heterocyclic ring containing a nitrogen bridgehead wherein said ring may also contain sulfur, oxygen, or an additional nitrogen atom, and may contain additional unsaturation.

  一种抑制有需要的人的单核细胞和/或巨噬细胞产生白细胞介素-1的方法，它包括向这种人施用有效的、抑制白细胞介素-1产生量的二芳基取代的咪唑与含有氮桥头原子的第二杂环融合，其中所述第二环也可含有硫、氧或另外的氮原子，并可含有另外的不饱和度。 本发明涉及一种抑制有需要的人体内的单核细胞或巨噬细胞产生肿瘤坏死因子（TNF）的方法，该方法包括向该哺乳动物施用有效的、可抑制 TNF 产生量的本文所述的式 (I) 化合物。式(II)化合物一般描述为二芳基取代的咪唑与含有氮桥头的第二个杂环融合，其中所述环还可含有硫、氧或额外的氮原子，并可含有额外的不饱和。