2,4-bis(4-N-morpholinophenyl)-6-phenyl(thiopyrylium) chloride | 1093845-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2,4-bis(4-N-morpholinophenyl)-6-phenyl(thiopyrylium) chloride
• 英文别名: 4-[4-[2-(4-Morpholin-4-ium-4-ylidenecyclohexa-2,5-dien-1-ylidene)-6-phenylthiopyran-4-yl]phenyl]morpholine;chloride
• CAS: 1093845-59-0
• 化学式: C₃₁H₃₁N₂O₂S*Cl
• 分子量: 531.118
• InChiKey: DYWYDMJTUUEROA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  50
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 Amberlite IRA-400 chloride exchange resin 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以88%的产率得到2,4-bis(4-N-morpholinophenyl)-6-phenyl(thiopyrylium) chloride
  参考文献：
  名称：

  Chalcogenopyrylium dyes as inhibitors/modulators of P-glycoprotein in multidrug-resistant cells

  摘要：

  A series of chalcogenopyrylium dyes were evaluated as modulators/inhibitors of P-glycoprotein (Pgp). Their ability to inhibit verapamil (VER)-dependent ATPase activity (IC50 values) in lipid-activated, mouse Cys-less mdr3 Pgp was determined. Their ability to promote calcein-AM (CAM) uptake in MDCKII-MDR1 cells and their capacity to be transported by Pgp in monolayers of MDCKII-MDR1 cells were also evaluated. The chalcogenopyrylium dyes promoted CAM uptake with values of EC50 between 5 x 10 (6) and 3.5 x 10 (5) M and 7 of the 9 dyes examined in transport studies were substrates for Pgp with efflux ratios (P-BA/AB) between 14 and 390. Binding of three compounds (1-S, 3-S, and 4-S) to Pgp was also assessed by fluorescence. These three thiopyrylium dyes showed increased fluorescence upon binding to Pgp, giving apparent binding constants, K-app, on the order of 10 (7) to 10 (6) M. Compound 8-Te was particularly intriguing since it appeared to influence Pgp at low micromolar concentrations as evidenced by its influence on VER-stimulated ATPase activity (IC50 of 1.2 x 10 (6) M), CAM uptake (EC50 of 5.4 x 10 (6) M), as well as [H-3]-vinblastine transport by Pgp in cells (IC50 of 4.3 x 10 (6) M) and within inside-out membrane vesicles (IC50 of 9.6 x 10 (6) M). Yet, Pgp did not influence the distribution of 8-Te in MDCKII-MDR1 monolayers suggesting that 8-Te may bind to an allosteric site. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.065