3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanenitrile | 1267327-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanenitrile
• 英文别名: 3-(2-Oxo-3-phenylmethoxypyridin-1-yl)propanenitrile；3-(2-oxo-3-phenylmethoxypyridin-1-yl)propanenitrile
• CAS: 1267327-26-3
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: ITBIKMNZBRVREU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanenitrile 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 39.0h， 生成 3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanamine
  参考文献：
  名称：

  掺入 3-Hydroxypyridin-2(1H)-one (3,2-HOPO) 配体的新合成方法：合成结构多样化的聚 3,2-HOPO 螯合剂

  摘要：

  3,2-HOPO 磺酰胺试剂3由市售的 2,3-二羟基吡啶分四步以良好的收率制备。磺酰胺3在碱存在下很容易与二溴化物进行选择性烷基化，或者可以使用 Mitsunobu 条件与醇偶联。这种亲核 3-羟基吡啶-2(1 H )-one (3,2-HOPO) 试剂的效用通过一些三-和四-3,2-HOPO 螯合剂的合成得到了证明。这种束缚 3,2-HOPO 配体的方法是独特且灵活的，如 3,2-HOPO/亚氨基羧酸螯合剂17的制备所示。 3-羟基吡啶-2(1 H )-一-合成-多齿螯合剂-混合配体螯合剂-磺酰胺

  DOI：

  10.1055/s-0030-1258337
• 作为产物：
  描述：

  吡啶-2,3-二醇 在 potassium carbonate 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 34.0h， 生成 3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanenitrile
  参考文献：
  名称：

  Multifunctional diamine AGE/ALE inhibitors with potential therapeutical properties against Alzheimer's disease

  摘要：

  An important part of pathogenesis of Alzheimer's disease (AD) is attributed to the contribution of AGE (Advanced Glycation Endproducts) and ALE (Advanced Lipid peroxidation Endproducts). In order to attenuate the progression of AD, we designed a new type of molecules that consist of two trapping parts for reactive carbonyl species (RCS) and reactive oxygen species (ROS), precursors of AGE and ALE, respectively. These molecules also chelate transition metals, the promoters of ROS formation. In this paper, synthesis of the new AGE/ALE inhibitors and evaluation of their physicochemical and biological properties (carbonyl trapping capacity, antioxidant activity, Cu2+-chelating capacity, cytotoxicity and protective effect against in vitro MGO-induced apoptosis in the model AD cell-line PC12) are described. It is found that compounds 40b and 51e possess promising therapeutic potentials for treating AD. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.069

文献信息

• VICINAL PRIMARY DIAMINES ASSOCIATED WITH METAL AND/OR FREE RADICAL CHELATION MOTIFS, AND ACTIVE AGAINST CARBONYL AND OXIDATIVE STRESS, AND USE THEREOF
  申请人：UNIVERSITE AMIENS PICARDIE JULES VERNE

  公开号：US20180201602A1

  公开（公告）日：2018-07-19

  The invention relates to compounds of Formula I: or the salts thereof, as well as the use thereof in the pharmaceutical, cosmetic or agrofood industry.

  该发明涉及公式I的化合物：或其盐，以及在制药、化妆品或农业食品工业中的使用。
• Vicinal primary diamines associated with metal and/or free radical chelation motifs, and active against carbonyl and oxidative stress, and use thereof
  申请人：UNIVERSITE AMIENS PICARDIE JULES VERNE

  公开号：US10464920B2

  公开（公告）日：2019-11-05

  The invention relates to compounds of Formula I: or the salts thereof, as well as the use thereof in the pharmaceutical, cosmetic or agrofood industry.

  本发明涉及式 I 的化合物： 或其盐类，以及它们在制药、化妆品或农产食品工业中的用途。
• DIAMINES PRIMAIRES VICINALES ASSOCIÉES À DES MOTIFS CHÉLATEURS DE MÉTAUX ET/OU DE RADICAUX LIBRES, ACTIVES CONTRE LES STRESS CARBONYLÉ ET OXYDANT ET LEUR UTILISATION
  申请人：Université Amiens Picardie Jules Verne

  公开号：EP3319950B1

  公开（公告）日：2021-11-03
• Multifunctional diamine AGE/ALE inhibitors with potential therapeutical properties against Alzheimer's disease
  作者：Elodie Lohou、N. André Sasaki、Agnès Boullier、Pascal Sonnet

  DOI：10.1016/j.ejmech.2016.04.069

  日期：2016.10

  An important part of pathogenesis of Alzheimer's disease (AD) is attributed to the contribution of AGE (Advanced Glycation Endproducts) and ALE (Advanced Lipid peroxidation Endproducts). In order to attenuate the progression of AD, we designed a new type of molecules that consist of two trapping parts for reactive carbonyl species (RCS) and reactive oxygen species (ROS), precursors of AGE and ALE, respectively. These molecules also chelate transition metals, the promoters of ROS formation. In this paper, synthesis of the new AGE/ALE inhibitors and evaluation of their physicochemical and biological properties (carbonyl trapping capacity, antioxidant activity, Cu2+-chelating capacity, cytotoxicity and protective effect against in vitro MGO-induced apoptosis in the model AD cell-line PC12) are described. It is found that compounds 40b and 51e possess promising therapeutic potentials for treating AD. (C) 2016 Elsevier Masson SAS. All rights reserved.
• New Synthetic Approach for the Incorporation of 3-Hydroxypyridin-2(1H)-one (3,2-HOPO) Ligands: Synthesis of Structurally Diverse Poly 3,2-HOPO Chelators
  作者：Hollie Jacobs、Aravamudan Gopalan、Jayanthi Arumugam、Hayley Brown

  DOI：10.1055/s-0030-1258337

  日期：2011.1

  using Mitsunobu conditions. The utility of this nucleophilic 3-hydroxypyridin-2(1H)-one (3,2-HOPO) reagent was demonstrated by the synthesis of some tris- and tetrakis-3,2-HOPO chelators. This approach for tethering 3,2-HOPO ligands is unique and flexible as shown by the preparation of 3,2-HOPO/iminocarboxylic acid chelator 17. 3-hydroxypyridin-2(1H)-one - synthesis - polydentate chelators - mixed

  3,2-HOPO 磺酰胺试剂3由市售的 2,3-二羟基吡啶分四步以良好的收率制备。磺酰胺3在碱存在下很容易与二溴化物进行选择性烷基化，或者可以使用 Mitsunobu 条件与醇偶联。这种亲核 3-羟基吡啶-2(1 H )-one (3,2-HOPO) 试剂的效用通过一些三-和四-3,2-HOPO 螯合剂的合成得到了证明。这种束缚 3,2-HOPO 配体的方法是独特且灵活的，如 3,2-HOPO/亚氨基羧酸螯合剂17的制备所示。 3-羟基吡啶-2(1 H )-一-合成-多齿螯合剂-混合配体螯合剂-磺酰胺