(2-Methylsulfanyl-thiazolo[5,4-b]quinolin-9-yl)-phenyl-amine | 690959-19-4

• 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: (2-Methylsulfanyl-thiazolo[5,4-b]quinolin-9-yl)-phenyl-amine
• 英文别名: 2-methylsulfanyl-N-phenyl-[1,3]thiazolo[5,4-b]quinolin-9-amine
• CAS: 690959-19-4
• 化学式: C₁₇H₁₃N₃S₂
• 分子量: 323.442
• InChiKey: HNKVGAPDGUSHRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Methylsulfanyl-thiazolo[5,4-b]quinolin-9-yl)-phenyl-amine 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 0.75h， 生成 9-anilino-2-(methylsulfonyl)thiazolo[5,4-b]quinoline
  参考文献：
  名称：

  新型9-苯胺噻唑并[5,4-b]喹啉衍生物的合成，细胞毒活性，DNA结合和分子对接研究

  摘要：

  制备了新颖的噻唑并[5，4- b ]喹啉衍生物，其在2-位带有或不带有（2-（氮杂环烷基）乙基）氨基取代基。评估了2位取代基对细胞毒活性，DNA嵌入和细胞毒特性的影响。带有脂族胺的2-位取代基有利于细胞毒性，而除去这些取代基则导致低或可忽略的细胞毒性。另外，新化合物在计算机上的计算机预测的结合模式与实验插层数据相关。这些结果表明2-位上的取代基对DNA嵌入性质的强烈影响。

  DOI：

  10.1007/s00044-016-1718-4
• 作为产物：
  描述：

  5-Anilino-2-methylsulfanyl-1,3-thiazole-4-carbonyl chloride 在 PPA 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 (2-Methylsulfanyl-thiazolo[5,4-b]quinolin-9-yl)-phenyl-amine
  参考文献：
  名称：

  Synthesis and evaluation of 9-anilinothiazolo[5,4-b]quinoline derivatives as potential antitumorals

  摘要：

  Five new 9-anilinothiazolo[5,4-b]quinoline derivatives (compounds 5, 7, 9, 10, 11) have been prepared. Some of the compounds were prepared by coupling properly substituted anilines to the novel compound 9-chloro-2-(methylthio)thiazolo[5,4-b]quinoline. Of these, compound 7 (9-anilino-2-[[2-(N,N-diethylamino)ethyl]amino]thiazolo[5,4-b]quinoline) showed the best cytotoxic activity in several cell lines. All compounds demonstrated DNA binding in nanomolar range. Compound 7 inhibited the C-14-thymidine incorporation into DNA. Results indicate that these derivatives deserve more considerations as potential antitumoral drugs. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.05.002

文献信息

• Synthesis, cytotoxic activity, DNA binding and molecular docking studies of novel 9-anilinothiazolo[5,4-b]quinoline derivatives
  作者：Francisco J. Reyes-Rangel、A. Kémish López-Rodríguez、Laura V. Pastrana-Cancino、Marco. A. Loza-Mejía、José D. Solano、Rogelio Rodríguez-Sotres、Alfonso Lira-Rocha

  DOI：10.1007/s00044-016-1718-4

  日期：2016.12

  effect of the substituent at 2-position on cytotoxic activity, DNA-intercalation and cytotoxic properties were evaluated. Substituents at 2-position bearing an aliphatic amine favored cytotoxicity, while removal of these substituents resulted in low or negligible cytotoxic properties. Additionally, the in silico predicted binding mode of the novel compounds into DNA correlated with the experimental intercalation

  制备了新颖的噻唑并[5，4- b ]喹啉衍生物，其在2-位带有或不带有（2-（氮杂环烷基）乙基）氨基取代基。评估了2位取代基对细胞毒活性，DNA嵌入和细胞毒特性的影响。带有脂族胺的2-位取代基有利于细胞毒性，而除去这些取代基则导致低或可忽略的细胞毒性。另外，新化合物在计算机上的计算机预测的结合模式与实验插层数据相关。这些结果表明2-位上的取代基对DNA嵌入性质的强烈影响。
• Synthesis and evaluation of 9-anilinothiazolo[5,4-b]quinoline derivatives as potential antitumorals
  作者：Pilar Rodríguez-Loaiza、Angelina Quintero、Rogelio Rodríguez-Sotres、José D Solano、Alfonso Lira-Rocha

  DOI：10.1016/j.ejmech.2003.05.002

  日期：2004.1

  Five new 9-anilinothiazolo[5,4-b]quinoline derivatives (compounds 5, 7, 9, 10, 11) have been prepared. Some of the compounds were prepared by coupling properly substituted anilines to the novel compound 9-chloro-2-(methylthio)thiazolo[5,4-b]quinoline. Of these, compound 7 (9-anilino-2-[[2-(N,N-diethylamino)ethyl]amino]thiazolo[5,4-b]quinoline) showed the best cytotoxic activity in several cell lines. All compounds demonstrated DNA binding in nanomolar range. Compound 7 inhibited the C-14-thymidine incorporation into DNA. Results indicate that these derivatives deserve more considerations as potential antitumoral drugs. (C) 2003 Elsevier SAS. All rights reserved.