1-(6-氯-2-羟基-4-苯基-喹啉-3-基)-乙酮 | 58375-08-9

• 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
• 中文名称: 1-(6-氯-2-羟基-4-苯基-喹啉-3-基)-乙酮
• 中文别名: 1-(6-氯-2-羟基-4-苯基喹啉-3-基)乙酮
• 英文名称: 3-acetyl-6-chloro-4-phenylquinolin-2(1H)-one
• 英文别名: 3-acetyl-6-chloro-4-phenyl-1H-quinolin-2-one；1-(6-Chloro-2-hydroxy-4-phenylquinolin-3-yl)ethanone
• CAS: 58375-08-9
• 化学式: C₁₇H₁₂ClNO₂
• mdl: MFCD01248820
• 分子量: 297.741
• InChiKey: AJBGMDVXSIBMLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-(6-氯-2-羟基-4-苯基-喹啉-3-基)-乙酮 在 potassium hydroxide 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.41h， 生成 4-(5-(4-bromophenyl)-3-(6-chloro-2-oxo-4-phenyl-1,2-dihydroquinolin-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoic acid
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-氨基-5-氯二苯甲酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以1.875 g的产率得到1-(6-氯-2-羟基-4-苯基-喹啉-3-基)-乙酮
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF TUMORS
  [FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE TUMEURS

  摘要：

  本发明涉及式(Ia)的化合物或药学上可接受的盐、水合物、溶剂合物、包合物、多晶型、立体异构体，还揭示了包含式(Ia)的化合物的药物组合物以及利用式(Ib)的化合物，特别是用于治疗破坏Rad51-BRCA2相互作用有益的疾病或紊乱的用途。

  公开号：

  WO2021116999A1

文献信息

• Robust synthesis of linear and angular furoquinolines using Rap–Stoermer reaction
  作者：Devadoss Karthik Kumar、Rayappan Rajkumar、Subramaniam Parameswaran Rajendran

  DOI：10.1007/s10593-016-1885-8

  日期：2016.5

  Rap–Stoermer reaction by conventional as well as microwave method that furnished an enhanced yield. Initially, we synthesized linear furo[2,3-b]quinolines from 3-acetyl-6-chloro-4-phenyl-1H-quinolin-2-one and three different α-halocarbonyl compounds: chloroacetophenone, ethyl chloroacetate, and chloroacetamide. The scope of the methodology was further extended to the synthesis of angular furo[3,2-c]quinolines

  我们通过常规和微波方法通过Rap-Stoermer反应合成了新颖的线性和有角呋喃喹啉，提高了收率。最初，我们从3-乙酰基-6-氯-4-苯基-1H-喹啉-2-酮和三种不同的α-卤代羰基化合物：氯乙酰苯，氯乙酸乙酯和氯乙酰胺合成了线性呋喃[2,3- b ]喹啉。通过利用3-乙酰基-4-羟基-1-甲基-1 H-喹啉-2-酮和α-卤代羰基化合物，该方法的范围进一步扩展到角呋喃[3,2- c ]喹啉的合成。
• Quinolinones as Inhibitors of Translation Initiation Complex
  申请人：Sanford-Burnham Medical Research Institute

  公开号：US20180044324A1

  公开（公告）日：2018-02-15

  Provided herein are compounds and pharmaceutical compositions comprising quinolinones. The quinolinones and compositions thereof are useful as eukaryotic translation initiation factor 4F (eIF4F) complex modulators.

  本文提供了含喹啉酮的化合物和药物组合物。这些喹啉酮及其组合物可用作真核翻译起始因子4F（eIF4F）复合物调节剂。
• Microwave-assisted solid acid-catalyzed synthesis of quinolinyl quinolinones and evaluation of their antibacterial, antioxidant activities
  作者：R. Subashini、Gangadhara Angajala、Kadirappa Aggile、F. Nawaz Khan

  DOI：10.1007/s11164-014-1575-z

  日期：2015.7

  Microwave-assisted montmorillonite K-10-catalyzed Friedlander synthesis of quinolinylquinolinones has been developed. The efficient and eco-friendly catalyst along with the convenience of the product isolation make this process an attractive alternative for the synthesis of target heterocycles. The synthesized products were confirmed by FTIR, 1H NMR, 13C NMR, and mass spectroscopic techniques. All the synthesized compounds showed good antibacterial property similar to standard Ampicillin and enhanced antioxidant activity.

  微波辅助蒙脱石K-10催化Friedlander合成喹啉基喹啉酮的方法已被开发。这种高效、环保的催化剂以及产品分离的便捷性使该过程成为合成目标杂环化合物的有吸引力的替代方案。合成的产物通过FTIR、1H NMR、13C NMR和质谱技术得到了确认。所有合成的化合物均显示出与标准氨苄西林相似的良好抗菌活性以及增强的抗氧化活性。
• Regioselective O-alkylation: synthesis of 1-{2-[(2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones
  作者：Machhindra Gund、S. Mohana Roopan、Fazlur-Rahman Nawaz Khan、Jong Sung Jin、Rajesh Kumar、A. Sudheer Kumar

  DOI：10.1007/s11164-011-0447-z

  日期：2012.3

  research on building blocks for synthesis of natural products. The nano-silver catalyst initiates O -alkylation of the amides by heteroalkyl halides. Reaction of equimolar 3-acetyl-6-chloro-4-phenylquinolin-2(1 H )-one and 2-chloro-3-(chloromethyl)quinolines in the presence of silver nanoparticles in DMSO solution under reflux condition leads to the formation of 1-1-[2-chloroquinolin-3-yl)methoxy]

  据报道，在我们最近对天然产物合成的基础材料研究的一部分中，在银纳米颗粒的存在下，使用各种亲电试剂对酰胺进行了高效且区域选择性的 O- 烷基化反应。纳米银催化剂通过杂烷基卤化物引发 酰胺的 O- 烷基化。在DMSO溶液中银纳米颗粒存在下，等摩尔3-乙酰基-6-氯-4-苯基喹啉-2（1 H ）-一和2-氯-3-（氯甲基）喹啉在回流条件下的反应导致形成1- 1- [2-氯喹啉-3-基）甲氧基] -6-氯-4-苯基喹啉-3-基}乙酮。
• [EN] METHODS AND COMPOSITIONS FOR INHIBITION OF BROMODOMAIN-CONTAINING PROTEINS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR L'INHIBITION DE PROTÉINES CONTENANT UN BROMODOMAINE
  申请人：CONVERGENE LLC

  公开号：WO2014159837A1

  公开（公告）日：2014-10-02

  The present invention relates to compounds that bind to and otherwise modulate the activity of bromodomain-containing proteins, to processes for preparing these compounds, to pharmaceutical compositions containing these compounds, and to methods of using these compounds for treating a wide variety of conditions and disorders.

  本发明涉及结合并调节含溴结构域蛋白活性的化合物，以及制备这些化合物的方法、含有这些化合物的药物组合物，以及利用这些化合物治疗各种疾病和疾病的方法。