9-chloro-2-(methylthio)thiazolo[5,4-b]quinoline | 690959-22-9

• 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-chloro-2-(methylthio)thiazolo[5,4-b]quinoline
• 英文别名: 9-Chloro-2-methylsulfanyl-[1,3]thiazolo[5,4-b]quinoline
• CAS: 690959-22-9
• 化学式: C₁₁H₇ClN₂S₂
• 分子量: 266.775
• InChiKey: VOKXEFZNLLTVMD-UHFFFAOYSA-N

物化性质

• 沸点：
  448.2±48.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-chloro-2-(methylthio)thiazolo[5,4-b]quinoline 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 N-[3-(2-Methylsulfanyl-thiazolo[5,4-b]quinolin-9-ylamino)-phenyl]-acetamide
  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
• 作为产物：
  描述：

  在 三氯氧磷 作用下， 生成 9-chloro-2-(methylthio)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

文献信息

• Synthesis, cytotoxic evaluation, and DNA binding of novel thiazolo[5,4-b]quinoline derivatives
  作者：Marco A. Loza-Mejía、Karina Maldonado-Hernández、Fernando Rodríguez-Hernández、Rogelio Rodríguez-Sotres、Ignacio González-Sánchez、Angelina Quintero、José D. Solano、Alfonso Lira-Rocha

  DOI：10.1016/j.bmc.2007.10.084

  日期：2008.2.1

  A series of novel alkylamino and 9-anilinothiazolo[5,4-b]quinolines were synthesized as potential antitumoral agents. The in vitro cytotoxicity of these compounds was evaluated on several cell lines. The inclusion of electron-withdrawn/acceptor hydrogen-bond groups at position 3' of the anilino ring and the presence of an alkylamino chain on the tricyclic framework (regardless of its position) seem

  合成了一系列新型的烷基氨基和9-苯胺基噻唑并[5,4-b]喹啉作为潜在的抗肿瘤药物。在几种细胞系上评估了这些化合物的体外细胞毒性。在苯胺基环的3'位上包含吸电子/受体氢键基团，并且三环骨架上存在烷基氨基链（无论其位置如何）似乎是与细胞毒性活性相关的结构特征。
• Synthesis, cytotoxic activity, DNA topoisomerase-II inhibition, molecular modeling and structure–activity relationship of 9-anilinothiazolo[5,4-b]quinoline derivatives
  作者：Marco A. Loza-Mejía、Susana Olvera-Vázquez、Karina Maldonado-Hernández、Teresita Guadarrama-Salgado、Ignacio González-Sánchez、Fernando Rodríguez-Hernández、José D. Solano、Rogelio Rodríguez-Sotres、Alfonso Lira-Rocha

  DOI：10.1016/j.bmc.2009.03.052

  日期：2009.5

  Some novel 9-anilinothiazolo[5,4-b]quinoline derivatives were synthesized and their cytotoxic activities were examined. The inhibition of some of the most active compounds over human topoisomerase II (Topo II) activity was assessed with the kDNA decatenation assay. The novel compounds differ in the substituents attached to the anilino ring, a dialkylamino alkylamino group, a saturated heterocyclic

  一些新颖的9-苯胺基氮杂[5,4- b合成了]喹啉衍生物，并检查了它们的细胞毒活性。用kDNA脱级测定法评估了一些最具活性的化合物对人类拓扑异构酶II（Topo II）活性的抑制作用。新化合物的不同之处在于与苯胺环相连的取代基，二烷基氨基烷基氨基基团，饱和杂环部分，位置2的甲硫基和在7位存在或不存在的氟原子。根据数据，在苯胺基环的4'-位具有二乙氨基丙基氨基基团和氯原子的化合物具有最高的细胞毒性。尽管偶极矩的方向和大小也对其细胞毒性有重要影响，但所有化合物的分子模型都表明疏水性和细胞毒性活性之间存在相关性。2-二烷基氨基烷基氨基取代基是柔性的，已知可以促进细胞膜的穿越；因此，最后的障碍可能是介导细胞毒性机制的限制步骤。另一方面，2-甲硫基衍生物的活性似乎更多地依赖于苯胺环的取代所带来的电子效应。介绍了合成，对癌细胞系的细胞毒性，对人类拓扑异构酶II的体外抑制作用，分子模型以及结构与活性之间
• 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.