2-tert-butyl-4-(2-(N,N-diethylaminocarbonyl)phenyl)-6-(4-(dimethylamino)phenyl)thiopyrylium bromide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-tert-butyl-4-(2-(N,N-diethylaminocarbonyl)phenyl)-6-(4-(dimethylamino)phenyl)thiopyrylium bromide
• 英文别名: [4-[6-Tert-butyl-4-[2-(diethylcarbamoyl)phenyl]thiopyran-2-ylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride
• 化学式: C₂₈H₃₅N₂OS*Cl
• 分子量: 483.118
• InChiKey: PTDYHRXQGNLYGR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-tert-butyl-6-[4-(dimethylamino)phenyl]-4H-thiopyran-4-one 、 N,N-二乙基苯甲酰胺 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 、 水 为溶剂， 反应 2.0h， 以45%的产率得到2-tert-butyl-4-(2-(N,N-diethylaminocarbonyl)phenyl)-6-(4-(dimethylamino)phenyl)thiopyrylium bromide
  参考文献：
  名称：

  Chalcogenopyrylium Compounds as Modulators of the ATP-Binding Cassette Transporters P-Glycoprotein (P-gp/ABCB1) and Multidrug Resistance Protein 1 (MRP1/ABCC1)

  摘要：

  Twenty-seven chalcogenopyrylium derivatives varying in the heteroatom of the pyrylium core and substituents at the 2-, 4-, and 6-positions were examined for their effect on human MRPI-mediated uptake of tritiated estradiol glucuronide into inside-out membrane vesicles, their affinity for and ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), and their ability to promote uptake of calcein AM and vinblastine in multidrug-resistant cells. Differences in their effects on MRP1 and P-gp activity were noted, and a second set of thiopyrylium compounds with systematic substituent changes was examined to refine these differences further. Derivatives with tert-butyl substituents in the 2- and 6-positions had the lowest inhibitory activity toward both transporters. Derivatives with thioamide functionality in the 4-position were more active against MRP1 than derivatives with amide functionality. Conversely, derivatives with amide functionality in the 4-position were more active in P-gp than derivatives with thioamide functionality.

  DOI：

  10.1021/jm3004398