3-chloro-N-(3-cyano-4-fluorophenyl)benzamide

• 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: 3-chloro-N-(3-cyano-4-fluorophenyl)benzamide
• 化学式: C₁₄H₈ClFN₂O
• 分子量: 274.682
• InChiKey: KXKRADWKTODIBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(3-cyano-4-fluorophenyl)benzamide 在 一水合肼 作用下， 反应 3.0h， 以46%的产率得到N-(3-amino-1H-indazol-5-yl)-3-chlorobenzamide
  参考文献：
  名称：

  The impact of binding site waters on the activity/selectivity trade-off of Janus kinase 2 (JAK2) inhibitors

  摘要：

  Structure based optimization of B39, an indazole-based low micromolar JAK2 virtual screening hit is reported. Analysing the effect of certain modifications on the activity and selectivity of the analogues suggested that these parameters are influenced by water molecules available in the binding site. Simulation of water networks in combination with docking enabled us to identify the key waters and to optimize our primary hit into a low nanomolar JAK2 lead with promising selectivity over JAK1.

  DOI：

  10.1016/j.bmc.2019.02.029
• 作为产物：
  描述：

  5-氨基-2-氟苯腈 、 3-氯苯甲酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以60%的产率得到3-chloro-N-(3-cyano-4-fluorophenyl)benzamide
  参考文献：
  名称：

  The impact of binding site waters on the activity/selectivity trade-off of Janus kinase 2 (JAK2) inhibitors

  摘要：

  Structure based optimization of B39, an indazole-based low micromolar JAK2 virtual screening hit is reported. Analysing the effect of certain modifications on the activity and selectivity of the analogues suggested that these parameters are influenced by water molecules available in the binding site. Simulation of water networks in combination with docking enabled us to identify the key waters and to optimize our primary hit into a low nanomolar JAK2 lead with promising selectivity over JAK1.

  DOI：

  10.1016/j.bmc.2019.02.029

文献信息

• The impact of binding site waters on the activity/selectivity trade-off of Janus kinase 2 (JAK2) inhibitors
  作者：Attila Egyed、Dávid Bajusz、György M. Keserű

  DOI：10.1016/j.bmc.2019.02.029

  日期：2019.4

  Structure based optimization of B39, an indazole-based low micromolar JAK2 virtual screening hit is reported. Analysing the effect of certain modifications on the activity and selectivity of the analogues suggested that these parameters are influenced by water molecules available in the binding site. Simulation of water networks in combination with docking enabled us to identify the key waters and to optimize our primary hit into a low nanomolar JAK2 lead with promising selectivity over JAK1.