N-{(4-氟苯基)[(4-甲基苯基)磺酰基]甲基}甲酰胺 | 165806-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-{(4-氟苯基)[(4-甲基苯基)磺酰基]甲基}甲酰胺
• 英文名称: N-[(4-fluorophenyl)[(4-methylphenyl)sulfonyl]methyl]formamide
• 英文别名: N-((4-fluorophenyl)(tosyl)methyl)formamide；4-fluorophenyl-tolylsulfonomethylformamide；N-[(4-Fluorophenyl)((4-methylphenyl)sulfonyl)methyl]formamide；N-[(4-fluorophenyl)-(4-methylphenyl)sulfonylmethyl]formamide
• CAS: 165806-94-0
• 化学式: C₁₅H₁₄FNO₃S
• 分子量: 307.345
• InChiKey: GPWSBFOCAYKXBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-{(4-氟苯基)[(4-甲基苯基)磺酰基]甲基}甲酰胺 在 三乙胺 、 三氯氧磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 23.0h， 生成 5-(4-fluoro-phenyl)-4-(4-pyridyl)-imidazole
  参考文献：
  名称：

  1-Substituted 4-Aryl-5-pyridinylimidazoles:  A New Class of Cytokine Suppressive Drugs with Low 5-Lipoxygenase and Cyclooxygenase Inhibitory Potency

  摘要：

  A series of 1-alkyl- or -aryl-4-aryl-5-pyridinylimidazoles (A) were prepared and tested for their ability to bind to a recently discovered protein kinase termed CSBP and to inhibit lipopolysaccharide (LPS)-stimulated TNF production in mice. The kinase, CSBP, appears to be involved in a signaling cascade initiated by a number of inflammatory stimuli and leading to the biosynthesis of the inflammatory cytokines IL-1 and TNF. Two related imidazole classes (B and C) had previously been reported to bind to CSBP and to inhibit LPS-stimulated human monocyte IL-1 and TNF production. The members of the earlier series exhibited varying degrees of potency as inhibitors of the enzymes of arachidonic acid metabolism, PGHS-1 and 5-LO. Several of the more potent CSBP ligands and TNF biosynthesis inhibitors among the present series of N-1-alkylated imidazoles (A) were tested as inhibitors of PGHS-1 and 5-LO and were found to be weak to inactive as inhibitors of these enzymes. One of the compounds, 9 (SE 210313) which lacked measureable activity as an inhibitor of the enzymes of arachidonate metabolism, and had good potency in the binding and in vivo TNF inhibition assays, was tested for antiarthritic activity in the AA rat model of arthritis. Compound 9 significantly reduced edema and increased bone mineral density in this model.

  DOI：

  10.1021/jm960415o
• 作为产物：
  描述：

  对氟苯甲醛 在 三甲基氯硅烷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 N-{(4-氟苯基)[(4-甲基苯基)磺酰基]甲基}甲酰胺
  参考文献：
  名称：

  溴代[3-乙基-4-芳基-5-（2-甲氧基吡啶-5-基）-1-丙基-1,3-二氢-2H-咪唑-2-亚甲基]金的合成，表征及生物学活性）复合体。

  摘要：

  溴[3-乙基-4-芳基-5-（2-甲氧基吡啶-5-基）-1-丙基-1,3-二氢-2H-咪唑-2-亚烷基]金（i）络合物（8a-h）合成并表征了在4-芳基环的不同位置具有甲氧基，甲基和氟取代基的化合物。确定了2-甲氧基吡啶-5-基残基和4-芳基环上的取代基与针对一系列细胞系的活性的相关性。尤其是针对顺铂耐药的卵巢癌细胞系A2780cis，活性最高的溴代[3-乙基-4-（4-甲氧基苯基）-5-（2-甲氧基吡啶-5-基）-1-丙基-1,3-二氢-2H-咪唑-2-亚烷基]金（i）络合物8c比金诺芬更具活性。它还可以更有效地抑制硫氧还蛋白还原酶，并诱导A2780cis细胞中大量的活性氧。此外，其对非癌性SV 80肺成纤维细胞的影响低于金诺芬。这一事实，再加上以MCF-7细胞为例确定的在肿瘤细胞中的高积累率，使得这种复合物成为了进一步研究的有趣候选者。

  DOI：

  10.1039/c9dt04824c

文献信息

• Formamide intermediates for the preparation of tri-substituted imidazole compounds with multiple therapeutic properties
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1227091A3

  公开（公告）日：2002-08-07

  The invention relates to a novel group of formamide compounds and a process for their preparation, useful in the preparation of tri-substituted imadazoles having multiple therapeutic properties.

  这项发明涉及一类新型的甲酰胺化合物及其制备方法，可用于制备具有多种治疗性能的三取代咪唑。
• Substituted imidazole compounds
  申请人：SmithKline Beecham Corporation

  公开号：US05716955A1

  公开（公告）日：1998-02-10

  Novel 1,4,5-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  新型1,4,5-取代咪唑化合物及其在治疗中作为细胞因子抑制剂使用的组合物。
• Imidazole compounds and compositions
  申请人：SmithKline Beecham Corporation

  公开号：US05739143A1

  公开（公告）日：1998-04-14

  Novel 1,4,5-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  新型1,4,5-取代咪唑化合物及其在治疗中作为细胞因子抑制剂使用的组合物。
• Imidazole compounds, compositions and use
  申请人：SmithKline Beecham Corporation

  公开号：US05658903A1

  公开（公告）日：1997-08-19

  Novel 1,4,5-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  1,4,5-取代咪唑化合物及其在治疗中作为细胞因子抑制剂使用的组合物。
• Process for making pyridyl and pyrimidine substituted imidazole compounds
  申请人：SmithKline Beecham Corporation

  公开号：US06218537B1

  公开（公告）日：2001-04-17

  1,4,5,-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  1,4,5-取代咪唑化合物和组合物，用于作为细胞因子抑制剂的治疗。