2-(苄基氨基)-N-羟基乙酰胺 | 847780-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(苄基氨基)-N-羟基乙酰胺
• 英文名称: 2-(benzylamino)-N-hydroxyacetamide
• 英文别名: N-benzylglycine hydroxamic acid；N~2~-Benzyl-N-hydroxyglycinamide
• CAS: 847780-38-5
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: MHMSTPWWRMNOQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苄基甘氨酸乙酯 在 羟胺 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 以96%的产率得到2-(苄基氨基)-N-羟基乙酰胺
  参考文献：
  名称：

  Efficient Continuous Flow Synthesis of Hydroxamic Acids and Suberoylanilide Hydroxamic Acid Preparation

  摘要：

  A continuous flow tubing reactor can be used to readily transform methyl or ethyl carboxylic esters into the corresponding hydroxamic acids. Flow rate, reactor volume, and temperature were optimized for the preparation of a small collection of hydroxamic acids. Synthetic advantages were identified as an increased reaction rate and higher product purity. This method was also successfully applied to the multistep preparation of suberoylanilide hydroxamic acid, a potent HDAC inhibitor used in anticancer therapy.

  DOI：

  10.1021/jo900144h

文献信息

• Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox
  作者：Paul Hermant、Damien Bosc、Catherine Piveteau、Ronan Gealageas、BaoVy Lam、Cyril Ronco、Matthieu Roignant、Hasina Tolojanahary、Ludovic Jean、Pierre-Yves Renard、Mohamed Lemdani、Marilyne Bourotte、Adrien Herledan、Corentin Bedart、Alexandre Biela、Florence Leroux、Benoit Deprez、Rebecca Deprez-Poulain

  DOI：10.1021/acs.jmedchem.7b01444

  日期：2017.11.9

  Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure–plasma stability relationships

  异羟肟酸是杰出的锌螯合基团，可用于设计各种治疗领域中的有效和选择性金属酶抑制剂。一些异羟肟酸显示出较高的血浆清除率，导致体内活性差，尽管它们在体外可能是非常有效的化合物。我们设计了一个由57名成员组成的异羟肟酸文库，以探索这些系列中结构与血浆的稳定性关系，并确定哪些酶和哪些药效团对血浆稳定性至关重要。芳基酯酶和羧酸酯酶被确定为异羟肟酸的主要代谢酶。最后，我们建议引入或删除结构特征以提高稳定性。因此，这项工作提供了第一个药物化学工具箱（实验程序和结构指导），用于评估和控制异羟肟酸的血浆稳定性，并充分发挥其作为体内药理探针和治疗剂的潜力。这项研究与临床前开发特别相关，因为它允许获得在人和啮齿动物模型中同样稳定的化合物。
• Compositions Having Antimycrobial Activity Including a Hydroxamate or a Hydroxamate and a Hydroxlyamine
  申请人：Kohn Harold

  公开号：US20080249181A1

  公开（公告）日：2008-10-09

  Antimycorbacterial compositions are disclosed comprising at least one hydroxamate or at least one hydroxamate and at least one hydroxylamine. The preferred ratio of hydroxamate to hydroxylamines is about 100:1 to about 1:1. A method for inhibiting mycobacterial growth is also disclosed comprising the step of administering the compositions of this invention to an animal including a human.

  公开了包含至少一种羟肟酸盐或至少一种羟肟酸盐和至少一种羟肟胺的抗分枝杆菌组合物。羟肟酸盐与羟肟胺的优选比例约为100：1至约1：1。还公开了一种抑制分枝杆菌生长的方法，包括将本发明的组合物给动物，包括人类。
• US7662856B2
  申请人：——

  公开号：US7662856B2

  公开（公告）日：2010-02-16
• [EN] COMPOSITIONS HAVING ANTIMYCROBIAL ACTIVITY INCLUDING A HYDROXAMATE OR A HYDROXAMATE AND A HYDROXYLAMINE<br/>[FR] COMPOSITIONS A ACTIVITE ANTIMYCOBACTERIENNE COMPRENANT UN HYDROXAMATE OU UN HYDROXAMATE ET UNE HYDROXYLAMINE
  申请人：UNIV HOUSTON SYSTEM

  公开号：WO2005020973A2

  公开（公告）日：2005-03-10

  Antimycorbacterial compositions are disclosed comprising at least one hydroxamate or at least one hydroxamate and at least one hydroxylamine. The preferred ratio of hydroxamate to hydroxylamines is about 100:1 to about 1:1. A method for inhibiting mycobacterial growth is also disclosed comprising the step of administering the compositions of this invention to an animal including a human.
• Efficient Continuous Flow Synthesis of Hydroxamic Acids and Suberoylanilide Hydroxamic Acid Preparation
  作者：Elena Riva、Stefania Gagliardi、Caterina Mazzoni、Daniele Passarella、Anna Rencurosi、Daniele Vigo、Marisa Martinelli

  DOI：10.1021/jo900144h

  日期：2009.5.1

  A continuous flow tubing reactor can be used to readily transform methyl or ethyl carboxylic esters into the corresponding hydroxamic acids. Flow rate, reactor volume, and temperature were optimized for the preparation of a small collection of hydroxamic acids. Synthetic advantages were identified as an increased reaction rate and higher product purity. This method was also successfully applied to the multistep preparation of suberoylanilide hydroxamic acid, a potent HDAC inhibitor used in anticancer therapy.