3,6-bis(N,N-dimethylamino)-9-(3-methoxyphenyl)telluroxanthylium bromide | 1158967-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,6-bis(N,N-dimethylamino)-9-(3-methoxyphenyl)telluroxanthylium bromide
• 英文别名: [6-(Dimethylamino)-9-(3-methoxyphenyl)telluroxanthen-3-ylidene]-dimethylazanium;bromide
• CAS: 1158967-33-9
• 化学式: Br*C₂₄H₂₅N₂OTe
• 分子量: 564.979
• InChiKey: IOAXPXMJTHRLNF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  15.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间溴苯甲醚 、 3,6-bis(dimethylamino)-9H-telluroxanthen-9-one 在 magnesium 、 氢溴酸 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 以94%的产率得到3,6-bis(N,N-dimethylamino)-9-(3-methoxyphenyl)telluroxanthylium bromide
  参考文献：
  名称：

  Rhodamine Inhibitors of P-Glycoprotein: An Amide/Thioamide “Switch” for ATPase Activity

  摘要：

  We have examined 46 tetramethylrosamine/rhodamine derivatives with structural diversity in the heteroatom of the xanthylium core, the amino substituents of the 3- and 6-positions, and the alkyl, aryl, or heteroaryl group at the 9-substituent. These compounds were examined for affinity and ATPase stimulation in isolated MDR3 CL P-gp and human P-gp-His(10), for their ability to promote uptake of calcein AM and vinblastine in multidrug-resistant MDCKII-MDR1 cells, and for transport in monolayers of MDCKII-MDR1 cells. Thioamide 31-S gave K-M of 0.087 mu M in human P-gp. Small changes in structure among this set of compounds affected affinity as well as transport rate (or flux) even though all derivatives examined were substrates for P-gp. With isolated protein, tertiary amide groups dictate high affinity and high stimulation while tertiary thioamide groups give high affinity and inhibition of ATPase activity. In MDCKII-MDR1 cells, the tertiary thioamide-containing derivatives promote uptake of calcein AM and have very slow passive, absorptive, and secretory rates of transport relative to transport rates for tertiary amide-containing derivatives. Thioamide 31-S promoted uptake of calcein AM and inhibited efflux of vinblastine with IC50's of similar to 2 mu M in MDCKII-MDR1 cells.

  DOI：

  10.1021/jm900253g

文献信息

• Rhodamine Inhibitors of P-Glycoprotein: An Amide/Thioamide “Switch” for ATPase Activity
  作者：Michael K. Gannon、Jason J. Holt、Stephanie M. Bennett、Bryan R. Wetzel、Tip W. Loo、M. Claire Bartlett、David M. Clarke、Geri A. Sawada、J. William Higgins、Gregory Tombline、Thomas J. Raub、Michael R. Detty

  DOI：10.1021/jm900253g

  日期：2009.5.28

  We have examined 46 tetramethylrosamine/rhodamine derivatives with structural diversity in the heteroatom of the xanthylium core, the amino substituents of the 3- and 6-positions, and the alkyl, aryl, or heteroaryl group at the 9-substituent. These compounds were examined for affinity and ATPase stimulation in isolated MDR3 CL P-gp and human P-gp-His(10), for their ability to promote uptake of calcein AM and vinblastine in multidrug-resistant MDCKII-MDR1 cells, and for transport in monolayers of MDCKII-MDR1 cells. Thioamide 31-S gave K-M of 0.087 mu M in human P-gp. Small changes in structure among this set of compounds affected affinity as well as transport rate (or flux) even though all derivatives examined were substrates for P-gp. With isolated protein, tertiary amide groups dictate high affinity and high stimulation while tertiary thioamide groups give high affinity and inhibition of ATPase activity. In MDCKII-MDR1 cells, the tertiary thioamide-containing derivatives promote uptake of calcein AM and have very slow passive, absorptive, and secretory rates of transport relative to transport rates for tertiary amide-containing derivatives. Thioamide 31-S promoted uptake of calcein AM and inhibited efflux of vinblastine with IC50's of similar to 2 mu M in MDCKII-MDR1 cells.