2,6-di-tert-butyl-4-phenylthiopyrylium bromide | 1375477-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 2,6-di-tert-butyl-4-phenylthiopyrylium bromide
• 英文别名: 2,6-Ditert-butyl-4-phenylthiopyrylium;bromide
• CAS: 1375477-54-5
• 化学式: Br*C₁₉H₂₅S
• 分子量: 365.377
• InChiKey: POAZPZMUZIDXRD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Δ-4H-2,6-di-tert-butylthiopyran-4-one 、 苯基溴化镁 在 氢溴酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以40%的产率得到2,6-di-tert-butyl-4-phenylthiopyrylium 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

文献信息

• Chalcogenopyrylium Compounds as Modulators of the ATP-Binding Cassette Transporters P-Glycoprotein (P-gp/<i>ABCB1</i>) and Multidrug Resistance Protein 1 (MRP1/<i>ABCC1</i>)
  作者：Sean P. Ebert、Bryan Wetzel、Robert L. Myette、Gwenaëlle Conseil、Susan P. C. Cole、Geri A. Sawada、Tip W. Loo、M. Claire Bartlett、David M. Clarke、Michael R. Detty

  DOI：10.1021/jm3004398

  日期：2012.5.24

  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.