9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-4-ylmethyl)-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide | 500279-28-7

• 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: 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-4-ylmethyl)-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide
• 英文别名: 9-Fluoro-7-hydroxy-3-methyl-5-oxo-N-[(pyridin-4-yl)methyl]-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide；7-fluoro-4-hydroxy-12-methyl-2-oxo-N-(pyridin-4-ylmethyl)-1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13)-tetraene-3-carboxamide
• CAS: 500279-28-7
• 化学式: C₂₀H₁₈FN₃O₃
• 分子量: 367.38
• InChiKey: XBZYVYXPWKSSJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氟-1,2,3,4-四氢-2-甲基喹啉 以 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-4-ylmethyl)-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide
  参考文献：
  名称：

  Identification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine–Quinolone Carboxamides

  摘要：

  Using a multiplexed, reporter gene-based, high throughput screen, we identified 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-3-ylmethyl)-2,3-dihydro-1H,SH-pyrido- [3,2,1-ij]quinoline-6-carboxamide as a TLR2 agonist. Preliminary structure-activity relationship studies on the carboxamide moiety led to the identification of analogues that induce chemokines and cytokines in a TLR2-dependent manner. These results represent new leads for the development of vaccine adjuvants.

  DOI：

  10.1021/acsmedchemlett.8b00540

文献信息

• Therapeutic compounds and methods of use thereof
  申请人：Regents of the University of Minnesota

  公开号：US11014921B2

  公开（公告）日：2021-05-25

  The invention provides a compound of formula I: or a salt thereof, wherein R1, R2, and R3 have any of the values described in the specification, as well as compositions comprising a compound of formula I. The compounds are useful as immunomodulating agents.

  本发明提供了一种式 I 的化合物： 或其盐，其中 R1、R2 和 R3 具有说明书中描述的任一值，以及包含式 I 化合物的组合物。这些化合物可用作免疫调节剂。
• 4-Hydroxy-2-quinolones. 108. N-R-amides of 9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid and their antitubercular activity
  作者：I. V. Ukrainets、L. V. Sidorenko、O. V. Gorokhova、O. V. Shishkin、A. V. Turov

  DOI：10.1007/s10593-006-0228-6

  日期：2006.9
• Identification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine–Quinolone Carboxamides
  作者：Ziwei Hu、Janardhan Banothu、Mallesh Beesu、Collin J. Gustafson、Michael J. H. Brush、Kathryn L. Trautman、Alex C. D. Salyer、Balaji Pathakumari、Sunil A. David

  DOI：10.1021/acsmedchemlett.8b00540

  日期：2019.1.10

  Using a multiplexed, reporter gene-based, high throughput screen, we identified 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-3-ylmethyl)-2,3-dihydro-1H,SH-pyrido- [3,2,1-ij]quinoline-6-carboxamide as a TLR2 agonist. Preliminary structure-activity relationship studies on the carboxamide moiety led to the identification of analogues that induce chemokines and cytokines in a TLR2-dependent manner. These results represent new leads for the development of vaccine adjuvants.