2-(4-methylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo-[1,2-a]-imidazole | 122454-68-6

• 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-(4-methylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo-[1,2-a]-imidazole
• 英文别名: 2-[4-(methylthio)phenyl]-3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole；5H-Pyrrolo(1,2-a)imidazole, 6,7-dihydro-2-(4-(methylthio)phenyl)-3-(4-pyridinyl)-；2-(4-methylsulfanylphenyl)-3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• CAS: 122454-68-6
• 化学式: C₁₈H₁₇N₃S
• 分子量: 307.419
• InChiKey: KRMOKGAZOYGDLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  56
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo-[1,2-a]-imidazole 在 盐酸 、 sodium periodate 作用下， 反应 18.0h， 以60%的产率得到2-[4-(甲基亚硫酰基)苯基]-3-(吡啶-4-基)-6,7-二氢-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
• 作为产物：
  描述：

  2-氯代-4'-氟苯乙酮 在 potassium tert-butylate 、 氧气 、 叔丁醇 作用下， 以 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 2-(4-methylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo-[1,2-a]-imidazole
  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

• A novel and efficient synthesis of a tetra-substituted imidazole
  作者：Jerome F. Hayes、Michael B. Mitchell、Garry Procter

  DOI：10.1016/s0040-4039(00)76529-4

  日期：1994.1

  A novel synthesis of a tetra-substituted imidazole is described. A key feature of the synthesis is the regioselective deprotonation of picolylpyrrolidinone 3 and the efficient reaction of this anion with an aryl nitrile to give the pyrrolidinoimidazole nucleus in a single step.

  描述了四取代的咪唑的新颖合成。合成的关键特征是吡啶甲基吡咯烷酮3的区域选择性去质子化，以及该阴离子与芳基腈的有效反应，可一步合成吡咯烷并咪唑核。
• 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：EP0306300A2

  公开（公告）日：1989-03-08

  Compounds comprising pyridyl and phenyl substituted pyrrolo[1,2-a]imidazole derivatives and pyridyl and phenyl substituted imidazo[1,2-a]pyridine derivatives, of formula wherein n = 0 or 1, and their use as 5-lipoxygenase pathway inhibitors.

  由吡啶基和苯基取代的吡咯并[1,2-a]咪唑衍生物和吡啶基和苯基取代的咪唑并[1,2-a]吡啶衍生物组成的化合物，其式为 其中 n = 0 或 1，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。