4,8,9-trimethylfuro[2,3-h]quinolin-2(1H)-one | 362519-02-6

• 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: 4,8,9-trimethylfuro[2,3-h]quinolin-2(1H)-one
• 英文别名: Furoquinolin-2-one,4,8,9-trimethyl；4,8,9-trimethyl-1H-furo[2,3-h]quinolin-2-one
• CAS: 362519-02-6
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: OREZZBPRDDFVTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  4,8,9-trimethylfuro[2,3-h]quinolin-2(1H)-one 在 氧气 、 tetraphenylporphyrin 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到8-acetyl-4-methyl-2-oxo-1,2-dihydroquinolin-7-yl acetate
  参考文献：
  名称：

  新的角状呋喃喹啉酮衍生物的合成、光氧化和表征，一种新的呋喃香豆素生物异构体

  摘要：

  通过羟基喹啉酮与α-卤代酮（如3-氯-2-丁酮和苯甲酰溴）的威廉姆森反应，然后用多磷酸（PPA）处理，合成了具有新骨架结构的角状呋喃喹啉酮衍生物。合成的角状呋喃喹啉酮在氯仿或二甲基甲酰胺中进行光氧化，并在四苯基卟啉 (TPP) 作为单线态氧敏化剂 ( 1 O 2 )存在下进行光氧化。光氧化反应通过[2+2]环加成反应提供光裂解产物。所有光产品都被分离出来并通过光谱分析进行了充分表征。

  DOI：

  10.1002/jccs.202000455
• 作为产物：
  描述：

  2,7-二羟基-4-甲基喹啉 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 28.0h， 生成 4,8,9-trimethylfuro[2,3-h]quinolin-2(1H)-one
  参考文献：
  名称：

  新的角状呋喃喹啉酮衍生物的合成、光氧化和表征，一种新的呋喃香豆素生物异构体

  摘要：

  通过羟基喹啉酮与α-卤代酮（如3-氯-2-丁酮和苯甲酰溴）的威廉姆森反应，然后用多磷酸（PPA）处理，合成了具有新骨架结构的角状呋喃喹啉酮衍生物。合成的角状呋喃喹啉酮在氯仿或二甲基甲酰胺中进行光氧化，并在四苯基卟啉 (TPP) 作为单线态氧敏化剂 ( 1 O 2 )存在下进行光氧化。光氧化反应通过[2+2]环加成反应提供光裂解产物。所有光产品都被分离出来并通过光谱分析进行了充分表征。

  DOI：

  10.1002/jccs.202000455

文献信息

• Novel angular furoquinolinones bearing flexible chain as antitumor agent: Design, synthesis, cytotoxic evaluation, and DNA-binding studies
  作者：Lijuan Xie、Xuhong Qian、Jingnan Cui、Yi Xiao、Kewei Wang、Peichun Wu、Liying Cong

  DOI：10.1016/j.bmc.2008.07.081

  日期：2008.9

  A series of novel N-substituted angular furoquinolinone derivatives were synthesized and evaluated for their antitumor activities against QGY, K562, HeLa, P388, and A549 cell lines in vitro. The derivatives bearing basic amino side chain showed an improved antitumor activity. Compound 5h N-(2-dimethylaminoethyl)-2-(4,8,9-trimethyl-2-oxo-2H-furo[2,3-h]quinolin-1-yl)-acetamide exhibited the highest activities against P388 and A549 cell lines, which are evidenced by the IC(50) values that are four to five fold lower than that for unsubstituted parent compound. DNA-binding experiments suggested that these derivatives bind to DNA through intercalation. (C) 2008 Elsevier Ltd. All rights reserved.
• DNA damage and biological effects induced by photosensitization with new N1-unsubstituted furo[2,3-h]quinolin-2(1H)-ones
  作者：Cristina Marzano、Adriana Chilin、Franco Bordin、Francarosa Baccichetti、Adriano Guiotto

  DOI：10.1016/s0968-0896(02)00145-1

  日期：2002.9

  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.
• Synthesis, photooxygenation, and characterization of new angular furoquinolinone derivatives, a new furocoumarin bioisoster
  作者：Sameh Elgogary、Hoda Abd Elghafar、Mohammad Mashaly

  DOI：10.1002/jccs.202000455

  日期：——

  via Williamson reaction of hydroxyquinolinones with α-haloketones, such as 3-chloro-2-butanone and phenacyl bromide, followed by treatment with polyphosphoric acid (PPA). The synthesized angular furoquinolinones were photooxygenated in chloroform or dimethyl formamide and in the presence of tetraphenylporphyrin (TPP) as a singlet oxygen sensitizer (1O2). The photooxygenation reactions furnished the

  通过羟基喹啉酮与α-卤代酮（如3-氯-2-丁酮和苯甲酰溴）的威廉姆森反应，然后用多磷酸（PPA）处理，合成了具有新骨架结构的角状呋喃喹啉酮衍生物。合成的角状呋喃喹啉酮在氯仿或二甲基甲酰胺中进行光氧化，并在四苯基卟啉 (TPP) 作为单线态氧敏化剂 ( 1 O 2 )存在下进行光氧化。光氧化反应通过[2+2]环加成反应提供光裂解产物。所有光产品都被分离出来并通过光谱分析进行了充分表征。