furo[2,3-h]quinolin-2(1H)-one | 362518-99-8

• 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: furo[2,3-h]quinolin-2(1H)-one
• 英文别名: furoquinolin-2-one；1H-furo[2,3-h]quinolin-2-one
• CAS: 362518-99-8
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: BAXNYJHQOLNLFI-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  furo[2,3-h]quinolin-2(1H)-one 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以70%的产率得到1-methylfuro[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-benzofuran-4(5H)-one 在 盐酸 、 铜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 喹啉 、 溶剂黄146 、 甲苯 为溶剂， 反应 102.0h， 生成 furo[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

文献信息

• PHOTOCHEMOTHERAPEUTIC HETEROCYCLIC AGENTS HAVING ANTIPROLIFERATIVE AND ANTINEOPLASTIC ACTIVITY
  申请人：Dall'Acqua Francesco

  公开号：US20120129884A1

  公开（公告）日：2012-05-24

  The present invention concerns the synthesis of new analogs of angelicins, pyrrolo [3,2-h]quinoline, for the treatment of pathologies having hyperproliferative character included those having neoplastic nature. The treatment is based on the combined action of pyrrolo [3,2-h]quinolines and UV-A light, through a clinical approach defined as PUVA (psoralen-UVA light). The most important feature of these compounds is that they exert their remarkable photoxicity without any DNA damage, which is the main origin of the side effects of the PUVA therapy.

  本发明涉及合成新的天使光素类似物，吡咯并[3,2-h]喹啉，用于治疗具有增殖性特征的病理，包括具有肿瘤性质的病理。治疗基于吡咯并[3,2-h]喹啉和紫外线-A光的联合作用，通过被定义为PUVA（苯酞-UVA光）的临床方法。这些化合物最重要的特点是它们在没有任何DNA损伤的情况下发挥显着的光毒性，这是PUVA治疗的副作用的主要来源。
• [EN] PHOTOCHEMOTHERAPEUTIC HETEROCYCLIC AGENTS HAVING ANTIPROLIFERATIVE AND ANTINEOPLASTIC ACTIVITY<br/>[FR] AGENTS HÉTÉROCYCLIQUES PHOTOCHIMIOTHÉRAPEUTIQUES AYANT UNE ACTIVITÉ ANTIPROLIFÉRATIVE ET ANTINÉOPLASIQUE
  申请人：UNIV PADOVA

  公开号：WO2011013159A1

  公开（公告）日：2011-02-03

  The present invention concerns the synthesis of new analogs of angelicins, pyrrolo[3,2-h]quinoline, for the treatment of pathologies having hyperproliferative character included those having neoplastic nature. The treatment is based on the combined action of pyrrolo[3,2-h]quinolines and UV-A light, through a clinical approach defined as PUVA (psoralen+UVA light). The most important feature of these compounds is that they exert their remarkable phototoxicity without any DNA damage, which is the main origin of the side effects of the PUVA therapy.
• 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.