N,N-diethylthiophene-2-carbothioamide | 1391088-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N,N-diethylthiophene-2-carbothioamide
• CAS: 1391088-50-8
• 化学式: C₉H₁₃NS₂
• 分子量: 199.341
• InChiKey: LXWIQQNQPNHJAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethylthiophene-2-carbothioamide 在 正丁基锂 、 N,N-二异丙基乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.53h， 生成 9-(5-(diethylcarbamoyl)thiophen-2-yl)selenorhodamine trifluoroacetate
  参考文献：
  名称：

  Selenorhodamine Photosensitizers for Photodynamic Therapy of P-Glycoprotein-Expressing Cancer Cells

  摘要：

  We examined a series of selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenorhodamine core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp) expressing cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their uptake into Colo-26 cells in the absence or presence of verapamil, for their dark and phototoxicity toward Colo-26 cells, for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their colocalization with mitochondrial specific agents in Colo-26 cells. Thioamide derivatives 16b and 18b were more effective photosensitizers than amide derivatives 15b and 17b. Selenorhodamine thioamides 16b and 18b were useful in a combination therapy to treat Colo-26 cells in vitro: a synergistic therapeutic effect was observed when Colo-26 cells were exposed to PDT and treatment with the cancer drug doxorubicin.

  DOI：

  10.1021/jm501259v
• 作为产物：
  描述：

  2-噻吩甲醛 、 二乙胺 在 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以49%的产率得到N,N-diethylthiophene-2-carbothioamide
  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

• [EN] METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS<br/>[FR] PROCÉDÉS ET COMPOSÉS DE PHOTOTHÉRAPIE FAISANT APPEL À DES PHOTOSENSIBILISANTS DE TYPE CHALCOGÉNORHODAMINE
  申请人：UNIV WAKE FOREST HEALTH SCIENCES

  公开号：WO2015187940A1

  公开（公告）日：2015-12-10

  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.

  一种从血细胞组合物中选择性消耗致病性T淋巴细胞的方法是通过(a)在体外将细胞组合物与有效量的活性化合物结合，然后(b)在体外用光辐照细胞，时间和强度足以选择性地杀死该细胞组合物中的致病性T淋巴细胞。还描述了作为这种活性化合物有用的硫属罗丹明光敏剂。
• Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)
  作者：Alexandra Orchard、Gregory A. Schamerhorn、Brandon D. Calitree、Geri A. Sawada、Tip W. Loo、M. Claire Bartlett、David M. Clarke、Michael R. Detty

  DOI：10.1016/j.bmc.2012.05.075

  日期：2012.7

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

  公开号：EP3152306A1

  公开（公告）日：2017-04-12
• Selenorhodamine Photosensitizers for Photodynamic Therapy of P-Glycoprotein-Expressing Cancer Cells
  作者：Jacqueline E. Hill、Michelle K. Linder、Kellie S. Davies、Geri A. Sawada、Janet Morgan、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1021/jm501259v

  日期：2014.10.23

  We examined a series of selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenorhodamine core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp) expressing cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their uptake into Colo-26 cells in the absence or presence of verapamil, for their dark and phototoxicity toward Colo-26 cells, for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their colocalization with mitochondrial specific agents in Colo-26 cells. Thioamide derivatives 16b and 18b were more effective photosensitizers than amide derivatives 15b and 17b. Selenorhodamine thioamides 16b and 18b were useful in a combination therapy to treat Colo-26 cells in vitro: a synergistic therapeutic effect was observed when Colo-26 cells were exposed to PDT and treatment with the cancer drug doxorubicin.