piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanethione | 1391088-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanethione
• CAS: 1391088-44-0
• 化学式: C₁₈H₂₆N₂S
• 分子量: 302.484
• InChiKey: KLQLKJPEDCILDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanethione 在 四甲基乙二胺 、 仲丁基锂 、 三乙胺 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 乙腈 为溶剂， 反应 4.17h， 生成 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-thiochromeno[3,2-g]quinolin-6(2H)-one
  参考文献：
  名称：

  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

  摘要：

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.075
• 作为产物：
  描述：

  N-(3-methylbut-2-enyl)-N-methylaniline 在 硫酸 、 sulfur 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanethione
  参考文献：
  名称：

  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

  摘要：

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.075