3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanamine | 499238-00-5

• 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]propanamine
• 英文别名: 1-(3-aminopropyl)-3-(benzyloxy)pyridin-2(1H)-one；1-(3-Aminopropyl)-3-phenylmethoxypyridin-2-one
• CAS: 499238-00-5
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: UHDCUBKNTXZQEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanamine 在 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 47.0h， 生成
  参考文献：
  名称：

  3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

  摘要：

  The HOPO vinyl sulfonamide 3 and the corresponding HOPO acrylamide 10 were easily prepared by short synthetic sequences. Investigation of the aza-Michael reactions of these linkers showed that they proceed at a higher rate in solvent systems containing water. The scope and limits of the aza-Michael reactions of 3 and 10 were examined. Reagents 3 and 10 reacted cleanly with piperazine to give the corresponding adducts which were deprotected to give the di-HOPO ligands 7 and 16. Reaction of HOPO acrylamide 10 with 1,4,7-triazacyclononane gave the tris-adduct 17 which was deprotected to give the desired tris-HOPO ligand 18. Overall, the aza-Michael reactions of 3 and 10 appear to be governed not only by the solvent but also by the nature of the amine and the solubility of the reaction intermediates. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.136
• 作为产物：
  描述：

  吡啶-2,3-二醇 在 sodium azide 、 硼烷四氢呋喃络合物 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 cesium fluoride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanamine
  参考文献：
  名称：

  制备 3-羟基-2-吡啶酮 (3,2-HOPO) 螯合剂的新方法 - 胺与新型亲电 3,2-HOPO 前体的反应。

  摘要：

  研究了新型亲电亚胺酯甲磺酸盐 5 的制备及其与伯胺和仲胺的反应。苯胺、叔丁胺和仲胺通过开环与 5 反应，以高产率得到相应的 HOPO 衍生物。这种方法的实用性已通过制备两种新的二-HOPO 衍生物 19 和 21 得到证明。 这种方法允许将 HOPO 配体引入到各种胺平台上，而不会同时形成酰胺键，并提供对 HOPO 的访问水溶性增加的螯合剂。

  DOI：

  10.1016/s0040-4039(02)01730-6

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。
• 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
• 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。
• Preparation of 3-benzyloxy-2-pyridinone functional linkers: tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators
  作者：Sarah Gibson、Rasika Fernando、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tet.2015.10.031

  日期：2015.12

  In contrast to 2,3-dihydroxypyridine, the 3-benzyloxy protected derivative, 2, undergoes facile alkylation at ambient temperatures with a variety of functionalized alkyl halides in good yields. This alkylation has been used to prepare a number of linkers that permit the attachment of 3,2-HOPO moieties onto various scaffolds using a wide range of coupling methods. The Mitsunobu reaction of 2 with representative alcohols was found to be of limited value due to competing O-alkylation that led to product mixtures. The phthalimide 3j can be converted in two steps to HOPO isocyanate 6 in excellent yields. Isocyanate 6 can be coupled to amines at room temperature or to alcohols in refluxing dichloroethane to obtain the corresponding urea or carbamate linked ligand systems. The coupling of isocyanate 6 with TREN followed by deprotection gave the tris-HOPO 10, an interesting target as it has both cationic and anionic binding sites. The HOPO hydroxylamine linker 11 was shown to be especially valuable as its coupling with carboxylic acids proceeds with the concomitant generation of an additional hydroxamate ligand moiety in the framework. The utility of this linker was shown by the preparation of two mixed HOPO-hydroxamate chelators, 16 and 19, based on the structure of desferrioxamine, a well-known trihydroxamate siderophore. (C) 2015 Elsevier Ltd. All rights reserved.
• 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