N,N'-([1,1'-biphenyl]-4,4'-diyl)bis(1-(4-fluorobenzoyl)piperidine-4-carboxamide) | 1597448-26-4

• 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: N,N'-([1,1'-biphenyl]-4,4'-diyl)bis(1-(4-fluorobenzoyl)piperidine-4-carboxamide)
• 英文别名: N,N'-([1,1'-biphenyl]-4,4'-diyl)bis(1-(4-fluorobenzoyl)piperidine-4-carboxamide) (13)；1-(4-fluorobenzoyl)-N-[4-[4-[[1-(4-fluorobenzoyl)piperidine-4-carbonyl]amino]phenyl]phenyl]piperidine-4-carboxamide
• CAS: 1597448-26-4
• 化学式: C₃₈H₃₆F₂N₄O₄
• 分子量: 650.725
• InChiKey: FXZCNYMOIJTMGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  联苯胺 在 三乙胺 、 三氟乙酸 、 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 N,N'-([1,1'-biphenyl]-4,4'-diyl)bis(1-(4-fluorobenzoyl)piperidine-4-carboxamide)
  参考文献：
  名称：

  Synthesis and biological evaluation of novel bis-aromatic amides as novel PTP1B inhibitors

  摘要：

  A series of bis-aromatic amides was designed, synthesized, and evaluated as a new class of inhibitors with IC50 values in the micromolar range against protein tyrosine phosphatase 1B (PTP1B). Among them, compound 15 displayed an IC50 value of 2.34 +/- 0.08 mu M with 5-fold preference over TCPTP. More importantly, the treatment of CHO/HIR cells with compound 15 resulted in increased phosphorylation of insulin receptor (IR), which suggested extensive cellular activity of compound 15. These results provided novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.015

文献信息

• Synthesis and biological evaluation of novel bis-aromatic amides as novel PTP1B inhibitors
  作者：Wen-Long Wang、Chao Huang、Li-Xin Gao、Chun-Lan Tang、Jun-Qing Wang、Min-Chen Wu、Li Sheng、Hai-Jun Chen、Fa-Jun Nan、Jing-Ya Li、Jia Li、Bainian Feng

  DOI：10.1016/j.bmcl.2014.03.015

  日期：2014.4

  A series of bis-aromatic amides was designed, synthesized, and evaluated as a new class of inhibitors with IC50 values in the micromolar range against protein tyrosine phosphatase 1B (PTP1B). Among them, compound 15 displayed an IC50 value of 2.34 +/- 0.08 mu M with 5-fold preference over TCPTP. More importantly, the treatment of CHO/HIR cells with compound 15 resulted in increased phosphorylation of insulin receptor (IR), which suggested extensive cellular activity of compound 15. These results provided novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs. (C) 2014 Elsevier Ltd. All rights reserved.