5,7-dimethoxy-2-phenyl-4-quinolone | 159188-33-7

• 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: 5,7-dimethoxy-2-phenyl-4-quinolone
• 英文别名: 5,7-dimethoxy-2-phenylquinoline-4(1H)-one；2-Phenyl-5,7-dimethoxyquinoline-4(1H)-one；5,7-dimethoxy-2-phenyl-1H-quinolin-4-one
• CAS: 159188-33-7
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: MARKNWBEXFOQHG-UHFFFAOYSA-N

物化性质

• 沸点：
  478.9±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-2-phenyl-4-quinolone 在 三乙胺 、 三氯氧磷 作用下， 反应 3.0h， 生成 5,7-dimethoxy-N,2-diphenylquinoline-4-amine
  参考文献：
  名称：

  新型4-氨基喹啉衍生物的合成及其抗肿瘤活性

  摘要：

  摘要通过使4-氯喹啉与相应的单/二烷基胺反应，合成了一系列新型的4-氨基喹啉衍生物作为抗肿瘤剂。在体外评估了这些化合物对HCT-116，A549，DU-145，HepG2和LN229细胞系的细胞毒性。结果表明，大多数合成的化合物显示出优异的细胞毒性，而5,7-二甲氧基-2-苯基-N-丙基喹啉-4-胺（6a）对HCT-116细胞显示出最强的细胞毒性。此外，6a可能会降低VEGF蛋白的表达。 图形概要已经描述了4-氨基喹啉衍生物的合成和抗肿瘤活性。

  DOI：

  10.1007/s00044-012-0283-8
• 作为产物：
  描述：

  3',5'-二甲氧基苯甲酰苯胺 在 四氯化锡 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 5,7-dimethoxy-2-phenyl-4-quinolone
  参考文献：
  名称：

  新型4-氨基喹啉衍生物的合成及其抗肿瘤活性

  摘要：

  摘要通过使4-氯喹啉与相应的单/二烷基胺反应，合成了一系列新型的4-氨基喹啉衍生物作为抗肿瘤剂。在体外评估了这些化合物对HCT-116，A549，DU-145，HepG2和LN229细胞系的细胞毒性。结果表明，大多数合成的化合物显示出优异的细胞毒性，而5,7-二甲氧基-2-苯基-N-丙基喹啉-4-胺（6a）对HCT-116细胞显示出最强的细胞毒性。此外，6a可能会降低VEGF蛋白的表达。 图形概要已经描述了4-氨基喹啉衍生物的合成和抗肿瘤活性。

  DOI：

  10.1007/s00044-012-0283-8

文献信息

• A Convenient Synthesis of Novel Phosphoramide Mustard Analogues of 2-Arylquinolone
  作者：Jinwei Yuan、Xiaolan Chen、Lingbo Qu、Shouren Zhang、Jiansha Lu、Yufen Zhao

  DOI：10.1080/10426500802625529

  日期：2009.10.30

  A series of novel phosphoramide mustard analogues of 2-arylquinolones are synthesized through a convenient and facile phosphorylated reaction, and their structures are elucidated by NMR, IR, and HR MS. The amino acid esters and phosphoryl nitrogen mustard are linked to 2-arylquinolone to improve their undesirable physicochemical and biological properties.

  通过简便易行的磷酸化反应合成了一系列2-芳基喹诺酮类的新型磷酰胺芥类似物，并通过NMR、IR和HR MS对其结构进行了阐明。氨基酸酯和磷酰氮芥与 2-芳基喹诺酮相连，以改善其不良的理化和生物学特性。
• Alkylation of 2-Phenyl-4-quinolones: Synthetic and Structural Studies.
  作者：Mohamed HADJERI、Anne-Marie MARIOTTE、Ahcène BOUMENDJEL

  DOI：10.1248/cpb.49.1352

  日期：——

  The alkylation of 2-phenyl-4-quinolones was investigated and showed that the N-alkylation versus O-alkylation is highly dependent on whether C-5 is hydroxylated or not. N-Alkylation is favoured by the presence of a 5-hydroxyl group. The synthetic and the NMR structural studies are reported.

  对2-苯基-4-喹啉酮的烷基化进行了研究，结果显示N-烷基化与O-烷基化高度依赖于C-5是否发生羟基化。5-羟基基团的存在促进了N-烷基化。报告了合成和NMR结构研究。
• Weakly Coordinating, Ketone-Directed (η⁵ -Pentamethylcyclopentadienyl)cobalt(III)- and (η⁵ -Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C−H Amidation of Arenes: A Route to Acridone Alkaloids
  作者：Sourav Sekhar Bera、Md Raja Sk、Modhu Sudan Maji

  DOI：10.1002/chem.201805376

  日期：2019.2.1

  monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high‐valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline

  芳香族酮，查尔酮，咔唑和二苯甲酮的弱配位，酮定向，区域选择性单酰胺化是通过使用高价钴和铑催化作用来获得许多生物学上重要的分子构件而实现的。该酰胺化反应与各种酮和一些酰胺化伙伴一起进行得很顺利。还研究了产物在各种杂环的合成中的应用，包括including啶，吲哚，喹啉，喹诺酮，喹啉酮和喹唑啉。通过这种方法，也可以完成基于cri啶酮的生物碱的总合成，即托达洛辛A，托达洛辛D和Arborinine，以及正式合成了丙烯醛和诺拉霉素。
• Antimitotic Activity of 5-Hydroxy-7-methoxy-2-phenyl-4-quinolones
  作者：Mohamed Hadjeri、Eva-Laure Peiller、Chantal Beney、Nabajyoti Deka、Martin A. Lawson、Charles Dumontet、Ahcène Boumendjel

  DOI：10.1021/jm049876x

  日期：2004.9.1

  We report the synthesis of 5-hydroxy-7-methoxy-2-phenyl-4-quinolones and their biological activity as antitumor agents. These molecules were initially evaluated for their ability to induce cell cycle arrest in the G2/M phase. Compounds that showed significant G2/M cell cycle arrest were tested for antiproliferative activity using both the MTT assay and the NCI in vitro 60 cell line human tumor screen. The 5-hydroxy-7-methoxy-2-phenyl-4-quinolone (3a) and 2-(3-fluorophenyl)-5-hydroxy-7-methoxy-4-quinolone (3f) were the most active in the cell cycle arrest test whereas 3f was found to be the most active in the MTT assay. In terms of structural requirements, we found that the presence of a 5-hydroxyl group, a 7-methoxy group, and an unsubstituted N1 were essential for the antimitotic activity. In accordance with the literature, a fluoro group at the 3'- or 2'-position and a methoxy or a chloro group at the 3'-position were found to be highly advantageous for both the cell cycle arrest and the antiproliferative activities.
• Synthesis of Novel Piperazine Phosphoramidate Analogues of 2-Arylquinolones
  作者：Zhibo Qu、Xiaolan Chen、Lingbo Qu、Jinwei Yuan、Huina Li、Yufen Zhao

  DOI：10.1080/10426500903120750

  日期：2010.6.30

  A series of novel piperazine phosphoramidate derivatives of 2-arylquinolones were synthesized to improve their physicochemical and biological properties through a facile phosphorylating reaction. Their structures were elucidated by NMR, ESI MS, and HRMS.