2-tert-butyl-6-(4-(dimethylamino)phenyl)-4-(5-(piperidine-1-carbonothioyl)thiophen-2-yl)thiopyrylium chloride | 1375477-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-tert-butyl-6-(4-(dimethylamino)phenyl)-4-(5-(piperidine-1-carbonothioyl)thiophen-2-yl)thiopyrylium chloride
• 英文别名: [4-[6-Tert-butyl-4-[5-(piperidine-1-carbothioyl)thiophen-2-yl]thiopyran-2-ylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride
• CAS: 1375477-76-1
• 化学式: C₂₇H₃₃N₂S₃*Cl
• 分子量: 517.223
• InChiKey: FFAPJZHLJJPMAQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  piperidin-1-yl(thiophen-2-yl)methanethione 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2-tert-butyl-6-(4-(dimethylamino)phenyl)-4-(5-(piperidine-1-carbonothioyl)thiophen-2-yl)thiopyrylium chloride
  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.