2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylic acid | 425620-61-7

• 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-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylic acid
• 英文别名: 2-oxo-1H-thieno[2,3-h]quinoline-3-carboxylic acid
• CAS: 425620-61-7
• 化学式: C₁₂H₇NO₃S
• 分子量: 245.258
• InChiKey: JJWADFCQUDEIDS-UHFFFAOYSA-N

物化性质

• 沸点：
  544.6±50.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylic acid 在 铜 、 potassium carbonate 作用下， 以 喹啉 、 丙酮 为溶剂， 反应 30.0h， 生成 2-methoxythieno[2,3-h]quinoline
  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 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 96.0h， 生成 2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylic acid
  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

文献信息

• Novel angular furo and thieno-quinolinones: synthesis and preliminary photobiological studies
  作者：Paola Fossa、Luisa Mosti、Giulia Menozzi、Cristina Marzano、Franca Baccichetti、Franco Bordin

  DOI：10.1016/s0968-0896(01)00328-5

  日期：2002.3

  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.