2'-methylthio-4'-fluoro-2-(anilinomethyl)imidazoline | 439291-58-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2'-methylthio-4'-fluoro-2-(anilinomethyl)imidazoline
• 英文别名: N-[4-Fluoro-2-(methylthio)phenyl]-4,5-dihydro-1H-imidazole-2-methanamine；N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-fluoro-2-methylsulfanylaniline
• CAS: 439291-58-4
• 化学式: C₁₁H₁₄FN₃S
• 分子量: 239.317
• InChiKey: XBBHVMXFPPVGMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-5-氟苯硫酚 在 2,6-二甲基吡啶 、 potassium tert-butylate 作用下， 以 乙醇 、 苯酚 为溶剂， 反应 2.5h， 生成 2'-methylthio-4'-fluoro-2-(anilinomethyl)imidazoline
  参考文献：
  名称：

  2-(Anilinomethyl)imidazolines as α₁ Adrenergic Receptor Agonists:  the Discovery of α_1a Subtype Selective 2‘-Alkylsulfonyl-Substituted Analogues

  摘要：

  A series of 2'-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of alpha-adrenergic receptor subtypes alpha(1a), alpha(1b), alpha(1d), alpha(2a), and alpha(2c). Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited alpha(1a) subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for alpha(1a) vs all other subtypes.

  DOI：

  10.1021/jm000542r

文献信息

• 2-(Anilinomethyl)imidazolines as α₁ Adrenergic Receptor Agonists:  the Discovery of α₁_a Subtype Selective 2‘-Alkylsulfonyl-Substituted Analogues
  作者：Stephen J. Hodson、Michael J. Bishop、Jason D. Speake、Frank Navas、Deanna T. Garrison、Eric C. Bigham、David L. Saussy,、James A. Liacos、Paul E. Irving、M. Jeffrey Gobel、Bryan W. Sherman

  DOI：10.1021/jm000542r

  日期：2002.5.1

  A series of 2'-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of alpha-adrenergic receptor subtypes alpha(1a), alpha(1b), alpha(1d), alpha(2a), and alpha(2c). Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited alpha(1a) subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for alpha(1a) vs all other subtypes.