N1-(2-(methylthio)thiazolo[5,4-b]quinolin-9-yl)benzene-1,3-diamine | 690959-23-0

• 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: N1-(2-(methylthio)thiazolo[5,4-b]quinolin-9-yl)benzene-1,3-diamine
• 英文别名: 3-N-(2-methylsulfanyl-[1,3]thiazolo[5,4-b]quinolin-9-yl)benzene-1,3-diamine
• CAS: 690959-23-0
• 化学式: C₁₇H₁₄N₄S₂
• 分子量: 338.457
• InChiKey: NVIRSWYJDAOKLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 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：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N1-(2-(methylthio)thiazolo[5,4-b]quinolin-9-yl)benzene-1,3-diamine 在 吡啶 作用下， 反应 14.0h， 以71.4%的产率得到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：

  4-(ethoxycarbonyl)-2-(methylthio)-5-(phenylamino)thiazole 在 盐酸 、 PPA 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 N1-(2-(methylthio)thiazolo[5,4-b]quinolin-9-yl)benzene-1,3-diamine
  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 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.