2-((3-cyanopyridin-2-yl)thio)-N-(4-fluorophenyl)acetamide | 915924-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((3-cyanopyridin-2-yl)thio)-N-(4-fluorophenyl)acetamide
• 英文别名: 2-[(3-Cyano-2-pyridinyl)thio]-N-(4-fluorophenyl)acetamide；2-(3-cyanopyridin-2-yl)sulfanyl-N-(4-fluorophenyl)acetamide
• CAS: 915924-50-4
• 化学式: C₁₄H₁₀FN₃OS
• 分子量: 287.317
• InChiKey: VEYDJJSXMYQQED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 2-((3-cyanopyridin-2-yl)thio)-N-(4-fluorophenyl)acetamide
  参考文献：
  名称：

  Discovery of cyanopyridine scaffold as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors through virtual screening and preliminary hit optimisation

  摘要：

  With the aim of discovering novel IDO1 inhibitors, a combined similarity search and molecular docking approach was employed to the discovery of 32 hit compounds. Testing the screened hit compounds has led to several novel submicromolar inhibitors. Especially for compounds LVS-019 with cyanopyridine scaffold, showed good IDO1 inhibitory activity. To discover more compounds with similar structures to LVS-019, a shape-based model was then generated on the basis of it and the second-round virtual screening was carried out leading to 23 derivatives. Molecular docking studies suggested a possible binding mode of LVS-019, which provides a good starting point for the development of cyanopyridine scaffold compounds as potent IDO1 inhibitor. To improve potency of these hits, we further designed and synthesised another 14 derivatives of LVS-019. Among these compounds, LBJ-10 showed improved potency compared to the hits and displayed comparable potency to the control GDC-0919 analogue. LBJ-10 can serve as ideal leads for further modifications as IDO1 inhibitors for cancer treatment.

  DOI：

  10.1080/14756366.2018.1480614