3-[2-(4'-tert-butylbiphenyl-4-yloxy)acetylamino]benzoic acid | 1360869-92-6

• 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-[2-(4'-tert-butylbiphenyl-4-yloxy)acetylamino]benzoic acid
• 英文别名: DLC27-14；3-[[2-[[4'-(1,1-Dimethylethyl)[1,1'-biphenyl]-4-yl]oxy]acetyl]amino]-benzoic acid；3-[[2-[4-(4-tert-butylphenyl)phenoxy]acetyl]amino]benzoic acid
• CAS: 1360869-92-6
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: QXBOQILKUMBONF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对溴苯氧乙酸 在 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 88.0h， 生成 3-[2-(4'-tert-butylbiphenyl-4-yloxy)acetylamino]benzoic acid
  参考文献：
  名称：

  A specific protein disorder catalyzer of HIV-1 Nef

  摘要：

  The HIV-1 auxiliary protein Nef is required for the onset and progression of AIDS in HIV-1-infected persons. Here, we have deciphered the mode of action of a second-generation inhibitor of Nef, DLC27-14, presenting a competitive IC(50) of similar to 16 mu M measured by MALDI-TOF experiments. Thermal protein denaturation experiments revealed a negative effect on stability of Nef in the presence of a saturating concentration of the inhibitor. The destabilizing action of DLC27-14 was confirmed by a HIV protease-based experiment, in which the protease sensitivity of DLC27-14-bound Nef was three times as high as that of apo Nef. The only compatible docking modes of action for DLC27-14 suggest that DLC27-14 promotes an opening of two a-helices that would destabilize the Nef core domain. DLC27-14 thus acts as a specific protein disorder catalyzer that destabilizes the folded conformation of the protein. Our results open novel avenues toward the development of next-generation Nef inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.051

文献信息

• A specific protein disorder catalyzer of HIV-1 Nef
  作者：Adrien Lugari、Sebastian Breuer、Thibault Coursindel、Sandrine Opi、Audrey Restouin、Xiaoli Shi、Alexis Nazabal、Bruce E. Torbett、Jean Martinez、Yves Collette、Isabelle Parrot、Stefan T. Arold、Xavier Morelli

  DOI：10.1016/j.bmc.2011.10.051

  日期：2011.12

  The HIV-1 auxiliary protein Nef is required for the onset and progression of AIDS in HIV-1-infected persons. Here, we have deciphered the mode of action of a second-generation inhibitor of Nef, DLC27-14, presenting a competitive IC(50) of similar to 16 mu M measured by MALDI-TOF experiments. Thermal protein denaturation experiments revealed a negative effect on stability of Nef in the presence of a saturating concentration of the inhibitor. The destabilizing action of DLC27-14 was confirmed by a HIV protease-based experiment, in which the protease sensitivity of DLC27-14-bound Nef was three times as high as that of apo Nef. The only compatible docking modes of action for DLC27-14 suggest that DLC27-14 promotes an opening of two a-helices that would destabilize the Nef core domain. DLC27-14 thus acts as a specific protein disorder catalyzer that destabilizes the folded conformation of the protein. Our results open novel avenues toward the development of next-generation Nef inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.