methyl 2-(2-fluoro-4′-nitro[1,1′-biphenyl]-4-yl)propanoate

• 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: methyl 2-(2-fluoro-4′-nitro[1,1′-biphenyl]-4-yl)propanoate
• 英文别名: methyl 2-(2-fluoro-4'-nitro-[1,1'-biphenyl]-4-yl)propanoate；Methyl 2-[3-fluoro-4-(4-nitrophenyl)phenyl]propanoate
• 化学式: C₁₆H₁₄FNO₄
• 分子量: 303.29
• InChiKey: ZFATYHLBFSTGEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-fluoro-4′-nitro[1,1′-biphenyl]-4-yl)propanoate 在 甲醇 、 sodium tetrahydroborate 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.0h， 生成 methyl 2-(4'-((5-chloro-2-hydroxybenzyl)amino)-2-fluoro[1,1'-biphenyl]-4-yl)propanoate
  参考文献：
  名称：

  Design, synthesis and evaluation of flurbiprofen-clioquinol hybrids as multitarget-directed ligands against Alzheimer’s disease

  摘要：

  A series of novel flurbiprofen-clioquinol hybrids were designed and synthesized as multifunctional agents for Alzheimer's disease therapy, and their potential was evaluated through various biological experiments. In vitro studies showed that most target compounds exhibited significant ability to inhibit self- and Cu2+-induced beta-amyloid aggregation. Furthermore, some target compounds, especially 7i and 7r, also showed biometal chelating abilities, antioxidant activity, anti-neuroinflammatory activity and appropriate BBB permeability. These biological activities indicated that the representative compound 7i and 7r might be promising multifunctional agents for AD treatment.

  DOI：

  10.1016/j.bmc.2020.115374
• 作为产物：
  描述：

  氟比洛芬 在 硫酸 、 硝酸 、 溶剂黄146 作用下， 反应 39.0h， 生成 methyl 2-(2-fluoro-4′-nitro[1,1′-biphenyl]-4-yl)propanoate
  参考文献：
  名称：

  Design, synthesis and evaluation of flurbiprofen-clioquinol hybrids as multitarget-directed ligands against Alzheimer’s disease

  摘要：

  A series of novel flurbiprofen-clioquinol hybrids were designed and synthesized as multifunctional agents for Alzheimer's disease therapy, and their potential was evaluated through various biological experiments. In vitro studies showed that most target compounds exhibited significant ability to inhibit self- and Cu2+-induced beta-amyloid aggregation. Furthermore, some target compounds, especially 7i and 7r, also showed biometal chelating abilities, antioxidant activity, anti-neuroinflammatory activity and appropriate BBB permeability. These biological activities indicated that the representative compound 7i and 7r might be promising multifunctional agents for AD treatment.

  DOI：

  10.1016/j.bmc.2020.115374

文献信息

• From N–H Nitration to Controllable Aromatic Mononitration and Dinitration─The Discovery of a Versatile and Powerful <i>N</i>-Nitropyrazole Nitrating Reagent
  作者：Tao Yang、Xiaoqian Li、Shuang Deng、Xiaotian Qi、Hengjiang Cong、Hong-Gang Cheng、Liangwei Shi、Qianghui Zhou、Lin Zhuang

  DOI：10.1021/jacsau.2c00413

  日期：2022.9.26

  nitration has become an important endeavor in both academia and industry. Herein, we report the identification of a powerful nitrating reagent, 5-methyl-1,3-dinitro-1H-pyrazole, from the N-nitro-type reagent library constructed using a practical N–H nitration method. This nitrating reagent behaves as a controllable source of the nitronium ion, enabling mild and scalable nitration of a broad range of (hetero)arenes

  硝基芳烃是非常有价值的有机化合物，长期以来被用作药物、农用化学品和炸药以及多种化学品的重要中间体。因此，芳香硝化的探索已成为学术界和工业界的一项重要工作。在此，我们报告了从N使用实用的 N-H 硝化方法构建的硝基型试剂库。这种硝化试剂可作为硝鎓离子的可控来源，能够对具有良好官能团耐受性的多种（杂）芳烃进行温和且可扩展的硝化。值得注意的是，我们的硝化方法可以通过操纵反应条件来控制，以选择性地提供单硝化或二硝化产物。这种方法在药物化学中的价值已经通过其对复杂生物相关分子的高效后期 C-H 硝化而得到了很好的证实。密度泛函理论 (DFT) 计算和初步机理研究表明，这种硝化试剂的强大功能和多功能性是由于协同的“硝基效应”和“甲基效应”。
• US3957861A
  申请人：——

  公开号：US3957861A

  公开（公告）日：1976-05-18
• US4009283A
  申请人：——

  公开号：US4009283A

  公开（公告）日：1977-02-22
• Design, synthesis and evaluation of flurbiprofen-clioquinol hybrids as multitarget-directed ligands against Alzheimer’s disease
  作者：Ziyi Yang、Qing Song、Zhongcheng Cao、Guangjun Yu、Zhuoling Liu、Zhenghuai Tan、Yong Deng

  DOI：10.1016/j.bmc.2020.115374

  日期：2020.4

  A series of novel flurbiprofen-clioquinol hybrids were designed and synthesized as multifunctional agents for Alzheimer's disease therapy, and their potential was evaluated through various biological experiments. In vitro studies showed that most target compounds exhibited significant ability to inhibit self- and Cu2+-induced beta-amyloid aggregation. Furthermore, some target compounds, especially 7i and 7r, also showed biometal chelating abilities, antioxidant activity, anti-neuroinflammatory activity and appropriate BBB permeability. These biological activities indicated that the representative compound 7i and 7r might be promising multifunctional agents for AD treatment.