2-(4-butylphenyl)quinolin-4(1H)-one | 1393827-39-8

• 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: 2-(4-butylphenyl)quinolin-4(1H)-one
• 英文别名: 2-(4-butylphenyl)-1H-quinolin-4-one
• CAS: 1393827-39-8
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: IUAHTDMRRTZBNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-acetylphenyl)-4-butylbenzamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到2-(4-butylphenyl)quinolin-4(1H)-one
  参考文献：
  名称：

  Evaluation of synthetic acridones and 4-quinolinones as potent inhibitors of cathepsins L and V

  摘要：

  Cathepsins, also known as lysosomal cysteine peptidases, are members of the papain-like peptidase family, involved in different physiological processes. In addition, cathepsins are implicated in many pathological conditions. This report describes the synthesis and evaluation of a series of N-arylanthranilic acids, acridones, and 4-quinolinones as inhibitors of cathepsins V and L The kinetics revealed that compounds of the classes of acridones are reversible competitive inhibitors of the target enzyme with affinities in the low micromolar range. They represent promising lead candidates for the discovery of novel competitive cathepsin inhibitors with enhanced selectivity and potency. On the other hand, 4-quinolinones were noncompetitive inhibitors and N-arylanthranilic acids were uncompetitive inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.002

文献信息

• Programmed Multiple C‐H Bond Functionalization of the Privileged 4‐hydroxyquinoline Template
  作者：Quentin Ronzon、Wei Zhang、Nicolas Casaretto、Elisabeth Mouray、Isabelle Florent、Bastien Nay

  DOI：10.1002/chem.202100929

  日期：2021.5.17

  reactive sites for diversity‐oriented functionalization, of which four were targeted. The C‐2 and C‐8 decorations were directed by an N‐oxide, before taking benefit of an O‐carbamoyl protection at C‐4 to perform a Fries rearrangement and install a carboxamide at C‐3. This also released the carbonyl group of 4‐quinolones, the ultimate directing group to functionalize position 5. Our study highlights the power

  裸杂环支架上取代基的引入可以通过定向的CH官能团选择性地实现。然而，仅偶尔以迭代的方式使用这种方法来装饰药用支架的各个位置以建立化学文库。我们在此报告了“编程的” 4-羟基喹啉的多种，位点选择性，金属催化的CH官能化。这个具有医学特权的模板确实具有多个响应站点，可用于面向多样性的功能化，其中四个是针对性的。在利用O之前，C-2和C-8装饰是由N氧化物控制的在C-4处进行氨基甲酰基保护，以进行Fries重组，并在C-3处安装甲酰胺。这也释放了4-喹诺酮的羰基，这是使位置5功能化的最终指导基团。我们的研究在证明了其强大的抗疟原性潜力之后，着重强调了多个CH功能化在生物学相关文库中产生多样性的能力。
• Supported palladium-catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes to access quinolin-4(1H)-ones
  作者：Jian-Shu Wang、Chenyu Li、Jun Ying、Tiefeng Xu、Wangyang Lu、Chuan-Ying Li、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2022.02.026

  日期：2022.4

  palladium supported on graphitic carbon nitride (Pd/g-CN) catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes has been developed for the expedite construction of quinolin-4(1)-one scaffolds. By using a low loading heterogeneous palladium catalyst, Mo(CO) as both the CO surrogate and the reductant, and nitroarenes as the nitrogen source, the reaction proceeded well to give a variety

  开发了一种负载于石墨氮化碳 (Pd/g-CN) 上的钯催化 2-溴硝基苯和炔烃的羰基环化，用于加快构建 quinolin-4(1)-one 支架。通过使用低负载量的多相钯催化剂、Mo(CO)作为CO替代物和还原剂、硝基芳烃作为氮源，反应进展顺利，得到了多种从良好到优异的喹啉-4(1)-酮。产量。
• Enhanced Selectivity in 4-Quinolone Formation: A Dual-Base System for Palladium-Catalyzed Carbonylative Cyclization with Fe(CO)5
  作者：Meng Guo、Dou Wu、Hongyu Yang、Xiao Zhang、Dong-Xu Xue、Weiqiang Zhang

  DOI：10.3390/molecules29040850

  日期：——

  resource facilitates the palladium-catalyzed carbonylative C-C coupling and subsequent intramolecular cyclization. By tuning the tandem kinetics of carbonylation and cyclization, this non-gaseous method achieves the successful synthesis of 22 distinct 4-quinolones with excellent yields. This is achieved through the three-component condensation of sub-stoichiometric amounts of Fe(CO)5 with 2-iodoaniline

  在 Pd 催化羰基化喹诺酮合成中使用气态 CO 提出了与安全性和精确压力控制相关的挑战。为此，开发了 4-喹诺酮化合物的简化非气态合成方法。本研究介绍了一种利用由哌嗪和三乙胺双碱系统激活的 Fe(CO)5 的可调 CO 释放系统。这种替代性液态 CO 资源有利于钯催化的羰基化 CC 偶联和随后的分子内环化。通过调整羰基化和环化的串联动力学，这种非气态方法以优异的产率成功合成了 22 种不同的 4-喹诺酮类药物。这是通过亚化学计量的 Fe(CO)5 与 2-碘苯胺和末端炔烃的三组分缩合来实现的。操作机理研究揭示了一种新颖的CO转移机制，可促进均相羰基环化，使该方法与传统技术区分开来。除了解决安全问题外，这种方法还提供了对选择性的精确控制，对药物研究以及药物和生物活性化合物的有效合成具有重大影响。
• Evaluation of synthetic acridones and 4-quinolinones as potent inhibitors of cathepsins L and V
  作者：Emerson F. Marques、Mauro A. Bueno、Patrícia D. Duarte、Larissa R.S.P. Silva、Ariani M. Martinelli、Caio Y. dos Santos、Richele P. Severino、Dieter Brömme、Paulo C. Vieira、Arlene G. Corrêa

  DOI：10.1016/j.ejmech.2012.04.002

  日期：2012.8

  Cathepsins, also known as lysosomal cysteine peptidases, are members of the papain-like peptidase family, involved in different physiological processes. In addition, cathepsins are implicated in many pathological conditions. This report describes the synthesis and evaluation of a series of N-arylanthranilic acids, acridones, and 4-quinolinones as inhibitors of cathepsins V and L The kinetics revealed that compounds of the classes of acridones are reversible competitive inhibitors of the target enzyme with affinities in the low micromolar range. They represent promising lead candidates for the discovery of novel competitive cathepsin inhibitors with enhanced selectivity and potency. On the other hand, 4-quinolinones were noncompetitive inhibitors and N-arylanthranilic acids were uncompetitive inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.