9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-thiochromeno[3,2-g]quinolin-6(2H)-one | 1391088-43-9

• 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: 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-thiochromeno[3,2-g]quinolin-6(2H)-one
• 英文别名: 9-(Dimethylamino)-1,4,4-trimethyl-2,3-dihydrothiochromeno[3,2-g]quinolin-6-one
• CAS: 1391088-43-9
• 化学式: C₂₁H₂₄N₂OS
• 分子量: 352.5
• InChiKey: ULEFOENTYQOYEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-diethylthiophene-2-carbothioamide 、 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-thiochromeno[3,2-g]quinolin-6(2H)-one 在 正丁基锂 、 二异丙胺 、 hexafluorophosphoric acid 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 0.53h， 以15%的产率得到6-(5-(diethylcarbamothioyl)thiophen-2-yl)-9-(dimethylamino)-1,4,4-trimethyl-2,3,4,6-tetrahydro-1H-thiochromeno[3,2-g]quinolin-6-ylium hexafluorophosphate
  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 四甲基乙二胺 、 硫酸 、 仲丁基锂 、 sulfur 、 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 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.67h， 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

文献信息

• METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS
  申请人：Wake Forest University Health Sciences

  公开号：US20170096636A1

  公开（公告）日：2017-04-06

  A method of selectively depleting pathogenic T lymphocytes from a blood cell composition is carried out by (a) combining the cell composition ex vivo with an active compound in an effective amount, and then (b) irradiating the cells with light ex vivo for a time and at an intensity sufficient to selectively kill pathogenic T lymphocytes in said cell composition. Chalcogenorhodamine photosensitizers useful as such active compounds are also described.