ethyl 6-chloro-4-hydroxy-7-methoxyquinoline-3-carboxylate

• 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: ethyl 6-chloro-4-hydroxy-7-methoxyquinoline-3-carboxylate
• 英文别名: ethyl 6-chloro-7-methoxy-4-oxo-1H-quinoline-3-carboxylate
• 化学式: C₁₃H₁₂ClNO₄
• 分子量: 281.696
• InChiKey: AAKUYWNSAMFENH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-chloro-4-hydroxy-7-methoxyquinoline-3-carboxylate 在 四(三苯基膦)钯 、 caesium carbonate 、 溶剂黄146 、 间氯过氧苯甲酸 、 三氯氧磷 、 三溴氧磷 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 10.0h， 生成 ethyl 2-(benzo[d][1,3]dioxol-5-yl)-6-chloro-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Lead Optimization of 3-Carboxyl-4(1H)-Quinolones to Deliver Orally Bioavailable Antimalarials

  摘要：

  Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

  DOI：

  10.1021/jm201642z
• 作为产物：
  描述：

  3-甲氧基-4-氯苯胺 以 二苯醚 、 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 6-chloro-4-hydroxy-7-methoxyquinoline-3-carboxylate
  参考文献：
  名称：

  Lead Optimization of 3-Carboxyl-4(1H)-Quinolones to Deliver Orally Bioavailable Antimalarials

  摘要：

  Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

  DOI：

  10.1021/jm201642z

文献信息

• [EN] COMPOUNDS FOR THE DEGRADATION OF BRD9 OR MTH1<br/>[FR] COMPOSÉS POUR LA DÉGRADATION DE BRD9 OU MTH1
  申请人：C4 THERAPEUTICS INC

  公开号：WO2020051235A1

  公开（公告）日：2020-03-12

  Compounds that degrade BRD9 or MTH1 via the ubiquitin proteasome pathway in a subject in need thereof for therapeutic applications are provided. The compounds provided have an E3 Ubiquitin Ligase targeting moiety (Degron) that is linked to a Targeting Ligand for BRD9 or MTH1.

  提供了通过泛素蛋白酶体途径降解BRD9或MTH1的化合物，用于治疗需要的受体。提供的化合物具有与BRD9或MTH1的靶向配体相连的E3泛素连接酶靶向基团（Degron）。
• COMPOUNDS FOR THE DEGRADATION OF BRD9 OR MTH1
  申请人：C4 Therapeutics, Inc.

  公开号：EP3846800A1

  公开（公告）日：2021-07-14
• Lead Optimization of 3-Carboxyl-4(1<i>H</i>)-Quinolones to Deliver Orally Bioavailable Antimalarials
  作者：Yiqun Zhang、Julie A. Clark、Michele C. Connelly、Fangyi Zhu、Jaeki Min、W. Armand Guiguemde、Anupam Pradhan、Lalitha Iyer、Anna Furimsky、Jason Gow、Toufan Parman、Farah El Mazouni、Margaret A. Phillips、Dennis E. Kyle、Jon Mirsalis、R. Kiplin Guy

  DOI：10.1021/jm201642z

  日期：2012.5.10

  Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.