N-(3-acetylphenyl)quinoline-2-carboxamide

• 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-(3-acetylphenyl)quinoline-2-carboxamide
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: AYTGRYMKIXIHMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-acetylphenyl)quinoline-2-carboxamide 在 N-溴代丁二酰亚胺(NBS) 、 silica gel 作用下， 以 甲醇 为溶剂， 以84%的产率得到N-(3-(2-bromoacetyl)phenyl)quinoline-2-carboxamide
  参考文献：
  名称：

  Tariquidar-Related Chalcones and Ketones as ABCG2 Modulators

  摘要：

  ABC transporters, including ABCG2, play a vital role in defending the human body against the vast range of xenobiotics. Even though this is beneficial for human health, these protein transporters have been implicated in the emerging resistance of cancer cells to a variety of structurally and functionally diverse anticancer drugs. In order to investigate their role in resistance, potent and selective ABCG2 modulators have been described in the literature. A leading class of modulators are the tariquidar analogues; however, their susceptibility to hydrolysis limits their applicable use. To overcome this, we synthesized a novel series of chalcone- and ketone-based compounds inspired by reported tariquidar analogues. Compounds were characterized and evaluated for their ABCG2 modulatory activity and ABC transporter selectivity. When compared to transporters ABCB1 and ABCC1, the chalcone-based compounds exhibited selectivity for ABCG2, while the ketone-based compounds showed only a slight preference for ABCG2. From the former series, chalcone 16d (UR-DP48) displayed similar activity to the reference fumitremorgin C, both producing comparable maximal effects. The compound exhibited marked antiproliferative activity, while cytotoxicity was less pronounced for the most active compound 17f from the ketone series. Chalcone-containing tariquidar analogues are promising modulators to aid in functional investigations of ABCG2 transporters.

  DOI：

  10.1021/acsmedchemlett.8b00289
• 作为产物：
  描述：

  间硝基苯乙酮 在 盐酸 、 铁粉 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 N-(3-acetylphenyl)quinoline-2-carboxamide
  参考文献：
  名称：

  Tariquidar-Related Chalcones and Ketones as ABCG2 Modulators

  摘要：

  ABC transporters, including ABCG2, play a vital role in defending the human body against the vast range of xenobiotics. Even though this is beneficial for human health, these protein transporters have been implicated in the emerging resistance of cancer cells to a variety of structurally and functionally diverse anticancer drugs. In order to investigate their role in resistance, potent and selective ABCG2 modulators have been described in the literature. A leading class of modulators are the tariquidar analogues; however, their susceptibility to hydrolysis limits their applicable use. To overcome this, we synthesized a novel series of chalcone- and ketone-based compounds inspired by reported tariquidar analogues. Compounds were characterized and evaluated for their ABCG2 modulatory activity and ABC transporter selectivity. When compared to transporters ABCB1 and ABCC1, the chalcone-based compounds exhibited selectivity for ABCG2, while the ketone-based compounds showed only a slight preference for ABCG2. From the former series, chalcone 16d (UR-DP48) displayed similar activity to the reference fumitremorgin C, both producing comparable maximal effects. The compound exhibited marked antiproliferative activity, while cytotoxicity was less pronounced for the most active compound 17f from the ketone series. Chalcone-containing tariquidar analogues are promising modulators to aid in functional investigations of ABCG2 transporters.

  DOI：

  10.1021/acsmedchemlett.8b00289

文献信息

• Synthesis, characterization of novel quinoline-2-carboxamide based chalcone derivatives and their molecular docking, photochemical studies
  作者：C. Thirumurugan、P. Vadivel、A. Lalitha、S. Lakshmanan

  DOI：10.1080/00397911.2020.1720737

  日期：2020.3.18

  Abstract Novel series of quinoline-2-carboxamide based chalcone derivatives (5a–g) have synthesized and characterized using 1H-NMR, 13C-NMR, Mass, and elemental analysis. In-silico molecular docking studies exhibited that synthesized compounds 5a and 5g are good binding energy (−8.46 kcal and −9.46 kcal) toward the essential requirements of targeted compounds for EGFR receptor-bearing quinazoline inhibitor

  摘要 使用 1H-NMR、13C-NMR、质量和元素分析合成并表征了新型系列喹啉-2-甲酰胺基查尔酮衍生物 (5a-g)。In-silico 分子对接研究表明，合成的化合物 5a 和 5g 具有良好的结合能（-8.46 kcal 和 -9.46 kcal），符合靶向化合物对带有 EGFR 受体的喹唑啉抑制剂（PDB ID：1M17（Lapitinib））的基本要求。UV-Vis 和荧光光谱测量对吸收、发射循环伏安法 (CV) 和最高占据分子轨道 (HOMO) 产生了显着影响。化合物 5g 的最低未占分子轨道 (LUMO) 值也与分子内电荷转移特征 (D-π-A) 一起得到确认。红移最大值 (510 nm) 是各种溶剂中随溶剂极性增加的发射光谱。图形概要