N-(2-acetyl-3-methoxyphenyl)benzamide | 776313-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-acetyl-3-methoxyphenyl)benzamide
• CAS: 776313-09-8
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: LLANCZCCUQRDAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  346.9±32.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-acetyl-3-methoxyphenyl)benzamide 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 20.0h， 生成 5-methoxy-2-phenyl-4-quinolone
  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：

  2'-甲氧基苯乙酮 、 3-phenyl-1,4,2-dioxazol-5-one 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.08h， 以65%的产率得到N-(2-acetyl-3-methoxyphenyl)benzamide
  参考文献：
  名称：

  酮配位的（η5-五甲基环戊二烯基）钴（III）和铑（III-五甲基环戊二烯基）铑（III）催化的芳烃CH-H酰胺化反应：弱配位：rid啶酮生物碱

  摘要：

  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。

  DOI：

  10.1002/chem.201805376

文献信息

• 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.
• 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。