methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate | 425620-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate
• CAS: 425620-51-5
• 化学式: C₁₃H₁₁NO₃S
• 分子量: 261.301
• InChiKey: HWOMNWUJSFYSTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate 在 盐酸 、 铜 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 喹啉 、 溶剂黄146 、 丙酮 、 甲苯 为溶剂， 反应 102.0h， 生成 1-methylthieno[2,3-h]quinolin-2(1H)-one
  参考文献：
  名称：

  Novel angular furo and thieno-quinolinones: synthesis and preliminary photobiological studies

  摘要：

  A number of new furo and thienoquinolinones carrying an electron-withdrawing function or unsubstituted at the position 3 were synthesized in order to obtain new potential photochemotherapeutic agents with increased anti proliferative activity and decreased toxic side effects. Our interest in studying the SAR of these derivatives also prompted us to investigate the influence of N-methylation on biological activity, by preparing N-methyl derivatives. The antiproliferative activity of all the newly synthesized compounds was evaluated and compared to 8-methoxypsoralen (8-MOP), the drug widely used in PUVA-therapy. The 3-unsubstituted thienoquinolinones were generally the most potent derivatives, followed by the furo-analogues. In particular. the unsubstituted thieno[2.3-h]quinoline-2(1H)one showed the highest activity in T2 bacteriophage, HeLa cells and Ehrlich cells tests. All the compounds, assayed on Escherichia coli WP2 TM9, showed a similar mutagenic activity, very close to that of 8-MOP. Except for 2-oxo-1,2-dihydrothieno[2.3-h]quinoline-3-carboxylic acid, which appeared to be very effective, all compounds generated singlet oxygen to slightly larger amounts when compared to 8-MOP. The N-methyl analogues only induced moderate skin erythemas on albino guinea pigs, while all other derivatives appeared to be entirely inactive. On the basis of these results, the unsubstituted thieno[2,3h]quinoline 2(1H)one seems to be the most interesting potential drug for PUVA photochemotherapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00328-5
• 作为产物：
  描述：

  5-[(dimethylamino)methylene]-6,7-dihydro-1-benzothiophen-4(5H)-one 、 氰乙酸甲酯 反应 24.0h， 以57%的产率得到methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate
  参考文献：
  名称：

  Novel angular furo and thieno-quinolinones: synthesis and preliminary photobiological studies

  摘要：

  A number of new furo and thienoquinolinones carrying an electron-withdrawing function or unsubstituted at the position 3 were synthesized in order to obtain new potential photochemotherapeutic agents with increased anti proliferative activity and decreased toxic side effects. Our interest in studying the SAR of these derivatives also prompted us to investigate the influence of N-methylation on biological activity, by preparing N-methyl derivatives. The antiproliferative activity of all the newly synthesized compounds was evaluated and compared to 8-methoxypsoralen (8-MOP), the drug widely used in PUVA-therapy. The 3-unsubstituted thienoquinolinones were generally the most potent derivatives, followed by the furo-analogues. In particular. the unsubstituted thieno[2.3-h]quinoline-2(1H)one showed the highest activity in T2 bacteriophage, HeLa cells and Ehrlich cells tests. All the compounds, assayed on Escherichia coli WP2 TM9, showed a similar mutagenic activity, very close to that of 8-MOP. Except for 2-oxo-1,2-dihydrothieno[2.3-h]quinoline-3-carboxylic acid, which appeared to be very effective, all compounds generated singlet oxygen to slightly larger amounts when compared to 8-MOP. The N-methyl analogues only induced moderate skin erythemas on albino guinea pigs, while all other derivatives appeared to be entirely inactive. On the basis of these results, the unsubstituted thieno[2,3h]quinoline 2(1H)one seems to be the most interesting potential drug for PUVA photochemotherapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00328-5