7-溴-2-苯基-4-喹啉醇 | 825620-24-4

• 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: 7-溴-2-苯基-4-喹啉醇
• 英文名称: 7-bromo-2-phenylquinolin-4-ol
• 英文别名: 7-bromo-2-phenyl-1H-quinolin-4-one
• CAS: 825620-24-4
• 化学式: C₁₅H₁₀BrNO
• 分子量: 300.154
• InChiKey: XRLIQZUPQOFEHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  7-溴-2-苯基-4-喹啉醇 在 三氯氧磷 作用下， 反应 4.0h， 生成 7-bromo-4-chloro-2-phenylquinoline
  参考文献：
  名称：

  [EN] QUINOLINE CGAS ANTAGONIST COMPOUNDS
  [FR] COMPOSÉS DE QUINOLÉINE ANTAGONISTES DE CGAS

  摘要：

  本公开提供了一种cGAS拮抗剂化合物，制备这些化合物的方法，含有这些化合物的药物组合物，以及它们在医学治疗中的用途。

  公开号：

  WO2022051634A1
• 作为产物：
  描述：

  3-氧代-3-苯基丙酰胺 在 m-bromoaniline hydrochloride 作用下， 以 二苯醚 、 甲苯 为溶剂， 反应 1.0h， 生成 7-溴-2-苯基-4-喹啉醇
  参考文献：
  名称：

  A Systematic Approach to the Optimization of Substrate-Based Inhibitors of the Hepatitis C Virus NS3 Protease:  Discovery of Potent and Specific Tripeptide Inhibitors

  摘要：

  The inadequate efficacy and tolerability of current therapies for the infectious liver disease caused by the hepatitis C virus have warranted significant efforts in the development of new therapeutics. We have previously reported competitive peptide inhibitors of the NS3 serine protease based on the N-terminal cleavage products of peptide substrates. A detailed study of the interactions of these substrate-based inhibitors with the different subsites of the serine protease active site led to the discovery of novel residues that increased the affinity of the inhibitors. In this paper, we report the combination of the best binding residues in a tetrapeptide series that resulted in extremely potent inhibitors that bind exquisitely well to this enzyme. A substantial increase in potency was obtained with the simultaneous introduction of a 7-methoxy-2-phenyl-4-quinolinoxy moiety at the gamma-position of the P2 proline and a tert-leucine as a P3 residue. The increase in potency allowed for the further truncation and led to the identification of tripeptide inhibitors. Structure activity relationship studies on this inhibitor series led to the identification of carbamate-containing tripeptides that are able to inhibit replication of subgenomic HCV RNA in cell culture with potencies below 1 muM. This inhibitor series has the potential of becoming antiviral agents for the treatment of HCV infections.

  DOI：

  10.1021/jm0494523

文献信息

• Selective Electrochemical Halogenation of Functionalized Quinolone
  作者：Meiqian Hu、Shuai Zhang、Changsheng Qin、Hongsheng Nie、Zhicheng Xiong、Xiaoyu Shi、Yumiao Zhao、Mingzhe Li、Shoucai Wang、Fanghua Ji、Guangbin Jiang

  DOI：10.1021/acs.joc.3c00876

  日期：2023.9.15

  This work describes an effective C3–H halogenation of quinoline-4(1H)-ones under electrochemical conditions, in which potassium halides serve as both halogenating agents and electrolytes. The protocol provides expedient access to different halogenated quinoline-4(1H)-ones with unique regioselectivity, broad substrate scope, and gram-scale synthesis employing convenient, environmentally friendly electrolysis

  这项工作描述了在电化学条件下喹啉-4(1 H )-酮的有效 C3-H 卤化，其中卤化钾既充当卤化剂又充当电解质。该方案提供了在不分开的电池中方便地获得不同的卤代喹啉-4(1 H )-酮的方法，这些卤代喹啉-4(1 H)-酮具有独特的区域选择性、广泛的底物范围以及采用方便、环保的电解进行的克级合成。机理研究表明，卤素自由基可以促进喹诺酮类药物中N-H键的活化。
• A Systematic Approach to the Optimization of Substrate-Based Inhibitors of the Hepatitis C Virus NS3 Protease:  Discovery of Potent and Specific Tripeptide Inhibitors
  作者：Montse Llinàs-Brunet、Murray D. Bailey、Elise Ghiro、Vida Gorys、Ted Halmos、Martin Poirier、Jean Rancourt、Nathalie Goudreau

  DOI：10.1021/jm0494523

  日期：2004.12.1

  The inadequate efficacy and tolerability of current therapies for the infectious liver disease caused by the hepatitis C virus have warranted significant efforts in the development of new therapeutics. We have previously reported competitive peptide inhibitors of the NS3 serine protease based on the N-terminal cleavage products of peptide substrates. A detailed study of the interactions of these substrate-based inhibitors with the different subsites of the serine protease active site led to the discovery of novel residues that increased the affinity of the inhibitors. In this paper, we report the combination of the best binding residues in a tetrapeptide series that resulted in extremely potent inhibitors that bind exquisitely well to this enzyme. A substantial increase in potency was obtained with the simultaneous introduction of a 7-methoxy-2-phenyl-4-quinolinoxy moiety at the gamma-position of the P2 proline and a tert-leucine as a P3 residue. The increase in potency allowed for the further truncation and led to the identification of tripeptide inhibitors. Structure activity relationship studies on this inhibitor series led to the identification of carbamate-containing tripeptides that are able to inhibit replication of subgenomic HCV RNA in cell culture with potencies below 1 muM. This inhibitor series has the potential of becoming antiviral agents for the treatment of HCV infections.
• [EN] QUINOLINE CGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS DE QUINOLÉINE ANTAGONISTES DE CGAS
  申请人：IMMUNESENSOR THERAPEUTICS INC

  公开号：WO2022051634A1

  公开（公告）日：2022-03-10

  The present disclosure provides compounds that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  本公开提供了一种cGAS拮抗剂化合物，制备这些化合物的方法，含有这些化合物的药物组合物，以及它们在医学治疗中的用途。