3-methoxy-4-methylquinolin-2(1H)-one | 861621-67-2

• 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: 3-methoxy-4-methylquinolin-2(1H)-one
• 英文别名: 3-methoxy-4-methyl-1H-quinolin-2-one
• CAS: 861621-67-2
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: BHMNBLCLFBTVDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-methylquinolin-2(1H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以8%的产率得到3-hydroxy-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1H)-one Series of Potent d-Amino Acid Oxidase (DAAO) Inhibitors

  摘要：

  3-Hydroxyquinolin-2(1H)-one (2) was discovered by high throughput screening in a functional assay to be a potent inhibitor of human DAAO, and its binding affinity was confirmed in a Biacore assay. Cocrystallization of 2 with the human DAAO enzyme defined the binding site and guided the design of new analogues. The SAR, pharmacokinetics, brain exposure, and effects on cerebellum D-serine are described. Subsequent evaluation against the rat DAAO enzyme revealed a divergent SAR versus the human enzyme and may explain the high exposures of drug necessary to achieve significant changes in rat or mouse cerebellum D-serine.

  DOI：

  10.1021/jm900128w
• 作为产物：
  描述：

  3-(2-nitro-phenyl)-2-oxo-butyric acid ethyl ester 在 溶剂黄146 、 锌 作用下， 生成 3-methoxy-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Kermack; Perkin; Robinson, Journal of the Chemical Society, 1921, vol. 119, p. 1612

  摘要：

  DOI：

文献信息

• Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1<i>H</i>)-one Series of Potent <scp>d</scp>-Amino Acid Oxidase (DAAO) Inhibitors
  作者：Allen J. Duplantier、Stacey L. Becker、Michael J. Bohanon、Kris A. Borzilleri、Boris A. Chrunyk、James T. Downs、Lain-Yen Hu、Ayman El-Kattan、Larry C. James、Shenping Liu、Jiemin Lu、Noha Maklad、Mahmoud N. Mansour、Scot Mente、Mary A. Piotrowski、Subas M. Sakya、Susan Sheehan、Stefanus J. Steyn、Christine A. Strick、Victoria A. Williams、Lei Zhang

  DOI：10.1021/jm900128w

  日期：2009.6.11

  3-Hydroxyquinolin-2(1H)-one (2) was discovered by high throughput screening in a functional assay to be a potent inhibitor of human DAAO, and its binding affinity was confirmed in a Biacore assay. Cocrystallization of 2 with the human DAAO enzyme defined the binding site and guided the design of new analogues. The SAR, pharmacokinetics, brain exposure, and effects on cerebellum D-serine are described. Subsequent evaluation against the rat DAAO enzyme revealed a divergent SAR versus the human enzyme and may explain the high exposures of drug necessary to achieve significant changes in rat or mouse cerebellum D-serine.
• Kermack; Perkin; Robinson, Journal of the Chemical Society, 1921, vol. 119, p. 1612
  作者：Kermack、Perkin、Robinson

  DOI：——

  日期：——