5-hydroxy-7-methoxy-2-phenyl-4-quinolone | 380501-40-6

• 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: 5-hydroxy-7-methoxy-2-phenyl-4-quinolone
• 英文别名: 5-hydroxy-7-methoxy-2-phenyl-1H-quinolin-4-one
• CAS: 380501-40-6
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: UIAGNRUVENWKST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-7-methoxy-2-phenyl-4-quinolone 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以46%的产率得到5-hydroxy-7-methoxy-1-methyl-2-phenyl-4-quinolone
  参考文献：
  名称：

  Alkylation of 2-Phenyl-4-quinolones: Synthetic and Structural Studies.

  摘要：

  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。

  DOI：

  10.1248/cpb.49.1352
• 作为产物：
  描述：

  3',5'-二甲氧基苯甲酰苯胺 在 potassium tert-butylate 、 三溴化硼 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 45.5h， 生成 5-hydroxy-7-methoxy-2-phenyl-4-quinolone
  参考文献：
  名称：

  Alkylation of 2-Phenyl-4-quinolones: Synthetic and Structural Studies.

  摘要：

  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。

  DOI：

  10.1248/cpb.49.1352

文献信息

• 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。
• [EN] A PROCESS FOR THE PREPARATION OF THE CORE STRUCTURE IN QUINOLONE AND NAPTHYRIDONE CLASS OF ANTIBIOTICS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LA STRUCTURE CENTRALE D'ANTIBIOTIQUES APPARTENANT AUX CLASSES QUINOLONE ET NAPHTHYRIDONE
  申请人：INDIAN INST TECHNOLOGY MADRAS

  公开号：WO2013157018A1

  公开（公告）日：2013-10-24

  This invention relates to quinolone- and naphthyridone derivatives represented by the general formula VII, and a process for their preparation using Baylis-Hillman adducts from substituted aromatic or hetero-aromatic aldehydes and amines of interest as the starting materials. After the tandem Aza-Michael addition and SNAr cyclization, the resulting 4-hydroxy-1,2,3,4-tetrahydroquinoline or 4-hydroxy-1, 2,3,4- tetrahydro-1,8-naphthyridine derivative was subjected to oxidation to get the quinolone or naphthyridone skeleton in one step in good to excellent yields.

  本发明涉及通式VII所代表的喹诺酮和萘啶酮衍生物，以及使用取代芳香族或杂芳香族醛和感兴趣的胺作为起始材料，从Baylis-Hillman加合物开始制备它们的过程。在串联的Aza-Michael加成和SNAr环化之后，所得的4-羟基-1,2,3,4-四氢喹啉或4-羟基-1,2,3,4-四氢-1,8-萘啶衍生物被氧化，从而在一步中以良好至优异的收率得到喹诺酮或萘啶酮骨架。
• 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.