4,6-Dimethyl-7-propargyloxyquinolin-2-one | 327024-71-5

• 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: 4,6-Dimethyl-7-propargyloxyquinolin-2-one
• CAS: 327024-71-5
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: TZKKVPVXYGTEJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,6-Dimethyl-7-propargyloxyquinolin-2-one 在 potassium carbonate 、 cesium fluoride 作用下， 以 丙酮 为溶剂， 反应 242.0h， 生成 1-(3'-Hydroxypropyl)-4,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one
  参考文献：
  名称：

  Photobiological properties of 1-(3′-hydroxypropyl)-4,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one, a new furocoumarin analogue

  摘要：

  A new furoquinolinone derivative, 1-(3'-hydroxypropyl)-4,6,8-trimethylfuro[2,3-h]quinolin-2(1H)-one (HPFQ, 4), was prepared, in which the nitrogen atom in position 1 carries a hydroxypropyl chain. The antiproliferative activity of HPFQ was studied in comparison with its analogue 1,4,6, 8-tetramethylfuro[2, 3-h]quinolin-2(1H)-one (FQ) and g-methoxypsoralen (8-MOP). By incubation in the dark. HPFQ, although retaining antitopoisomerase II activity, appeared less effective than FQ. Upon UVA irradiation, HPFQ produced little amounts of singlet oxygen, but detectable levels of superoxide anion; like FQ, HPFQ induced numbers of DNA-protein cross-links, but no interstrand cross-links in mammalian cells. The HPFQ phototoxicity was comparable to that of FQ and g-MOP, while mutagenic activity, scored in two Escherichia coli strains, seemed much less remarkable. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00091-4
• 作为产物：
  描述：

  4,6-dimethyl-7-hydroxyquinolin-2-one 、 3-氯丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 40.0h， 以40%的产率得到4,6-Dimethyl-7-propargyloxyquinolin-2-one
  参考文献：
  名称：

  DNA damage and biological effects induced by photosensitization with new N1-unsubstituted furo[2,3-h]quinolin-2(1H)-ones

  摘要：

  New furoquinolinones unsubstituted at the N-1 position were prepared and their photobiological activities we re studied in comparison with 4.6.8.9-tetramethylfuro[2,3-h]quinotin-2(1H)-one (HFQ) and 8-MOP. The anti-proliferative activity of furoquinolinones 3a-f was tested upon UVA irradiation in mammalian cells, studying DNA synthesis and clonal growth capacity. and in micro-organisms, evaluating T2 infectivity. Almost all compounds appeared to be more active than 8-MOP, and free of any mutagenic activity and skin phototoxicity. Among them, compound 3b was the most effective one. Similarly to HFQ, compound 3b appeared to be very active also in DNA damaging, forming monoadducts and DPCL - 0. but no ISC and DPCL > 0, both responsible for furocoumarin genotoxicity and phototoxicity. Moreover, Ehrlich ascites cells, photoinactivated by the new furoquinolinone 3b and injected into recipient mice. proved to be capable of inducing protection against a successive challenge performed with the same tumor cells. For all these features. 3b seemed to be a new promising potential drug for PUVA therapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00145-1