5,6,7-trimethoxy-2-phenyl-4(1H)-quinolone | 159188-35-9

• 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: 5,6,7-trimethoxy-2-phenyl-4(1H)-quinolone
• 英文别名: 5,6,7-Trimethoxy-2-phenylquinolin-4(1H)-one；5,6,7-trimethoxy-2-phenyl-1H-quinolin-4-one
• CAS: 159188-35-9
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: NDPXPFMHGJLPAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6,7-trimethoxy-2-phenyl-4(1H)-quinolone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-Hydroxy-6,7-dimethoxy-2-phenyl-1H-quinolin-4-one
  参考文献：
  名称：

  Antimitotic Activity of 5-Hydroxy-7-methoxy-2-phenyl-4-quinolones

  摘要：

  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.

  DOI：

  10.1021/jm049876x
• 作为产物：
  描述：

  (Z)-ethyl 3-(methylamino)-3-phenylacrylate 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 38.0h， 生成 5,6,7-trimethoxy-2-phenyl-4(1H)-quinolone
  参考文献：
  名称：

  Toda, Jun; Fuse, Takako; Kishikawa, Etsuko, Heterocycles, 1994, vol. 38, # 9, p. 2091 - 2098

  摘要：

  DOI：

文献信息

• α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors
  作者：Hong Gao、Jun Kawabata

  DOI：10.1016/j.bmc.2004.12.010

  日期：2005.3.1

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.
• Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2′-aminoacetophenones
  作者：Derong Ding、Xin Li、Xin Wang、Yongli Du、Jingkang Shen

  DOI：10.1016/j.tetlet.2006.07.117

  日期：2006.9

  The syntheses of a diverse set of 2-aryl-4-quinolone derivatives were achieved by exposing corresponding acylated 2'aminoacetophenones to microwave irradiation in the presence of NaOH. The microwave accelerated cyclizations were complete within 10-22 min at 120 degrees C giving 57-95% isolated yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Toda Jun, Fuse Takako, Kishikawa Etsuko, Ando Naoko, Negishi Rumi, Horigu+, Heterocycles, 38 (1994) N 9, S 2091-2097
  作者：Toda Jun, Fuse Takako, Kishikawa Etsuko, Ando Naoko, Negishi Rumi, Horigu+

  DOI：——

  日期：——
• Discovery of quinazolin-4-one-based non-covalent inhibitors targeting the severe acute respiratory syndrome coronavirus 2 main protease (SARS-CoV-2 Mpro)
  作者：Kuojun Zhang、Tianyu Wang、Maotian Li、Mu Liu、He Tang、Lin Wang、Ke Ye、Jiamei Yang、Sheng Jiang、Yibei Xiao、Youhua Xie、Meiling Lu、Xiangyu Zhang

  DOI：10.1016/j.ejmech.2023.115487

  日期：2023.9
• 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.