(2-oxo-1,2-dihydroquinolin-6-yl)boronic acid | 1092790-24-3

• 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-oxo-1,2-dihydroquinolin-6-yl)boronic acid
• 英文别名: (2-oxo-1H-quinolin-6-yl)boronic acid
• CAS: 1092790-24-3
• 化学式: C₉H₈BNO₃
• 分子量: 188.978
• InChiKey: WQYHFDIBGLFSRR-UHFFFAOYSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-oxo-1,2-dihydroquinolin-6-yl)boronic acid 在 二(三叔丁基膦)钯 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Discovery of a Potent Parenterally Administered Factor XIa Inhibitor with Hydroxyquinolin-2(1H)-one as the P2′ Moiety

  摘要：

  Structure-activity relationship optimization of phenylalanine P1' and P2' regions with a phenylimidazole core resulted in a series of potent FXIa inhibitors. Introducing 4-hydroxyquinolin-2-one as the P2' group enhanced FXIa affinity and metabolic stability. Incorporation of an N-methyl piperazine amide group to replace the phenylalanine improved both FXIa potency and aqueous solubility. Combination of the optimization led to the discovery of FXIa inhibitor 13 with a FXIa K-i of 0.04 nM and an aPTT EC2x of 1.0 mu M. Dose-dependent efficacy (EC50 of 0.53 mu M) was achieved in the rabbit ECAT model with minimal bleeding time prolongation.

  DOI：

  10.1021/acsmedchemlett.5b00066
• 作为产物：
  描述：

  6-溴喹啉-2-酮 、 联硼酸新戊二醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到(2-oxo-1,2-dihydroquinolin-6-yl)boronic acid
  参考文献：
  名称：

  Discovery of a Potent Parenterally Administered Factor XIa Inhibitor with Hydroxyquinolin-2(1H)-one as the P2′ Moiety

  摘要：

  Structure-activity relationship optimization of phenylalanine P1' and P2' regions with a phenylimidazole core resulted in a series of potent FXIa inhibitors. Introducing 4-hydroxyquinolin-2-one as the P2' group enhanced FXIa affinity and metabolic stability. Incorporation of an N-methyl piperazine amide group to replace the phenylalanine improved both FXIa potency and aqueous solubility. Combination of the optimization led to the discovery of FXIa inhibitor 13 with a FXIa K-i of 0.04 nM and an aPTT EC2x of 1.0 mu M. Dose-dependent efficacy (EC50 of 0.53 mu M) was achieved in the rabbit ECAT model with minimal bleeding time prolongation.

  DOI：

  10.1021/acsmedchemlett.5b00066

文献信息

• Orally Bioavailable Quinoxaline Inhibitors of 15-Prostaglandin Dehydrogenase (15-PGDH) Promote Tissue Repair and Regeneration
  作者：Bin Hu、Kosuke Toda、Xiaoyu Wang、Monika I. Antczak、Julianne Smith、Sophie Geboers、Gen Nishikawa、Hongyun Li、Dawn Dawson、Stephen Fink、Amar B. Desai、Noelle S. Williams、Sanford D. Markowitz、Joseph M. Ready

  DOI：10.1021/acs.jmedchem.2c01299

  日期：2022.11.24