2-(p-methylphenoxy)acetohydroxamic acid | 13359-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(p-methylphenoxy)acetohydroxamic acid
• 英文别名: N-hydroxy-2-(4-methylphenoxy)acetamide；N-hydroxy-3-(p-tolyloxy)acetamide；2-p-tolyloxy-acetohydroxamic acid；2-p-Tolyloxy-acetohydroxamsaeure
• CAS: 13359-20-1
• 化学式: C₉H₁₁NO₃
• mdl: MFCD16302131
• 分子量: 181.191
• InChiKey: ROCWONVWEMBXNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-methylphenoxy)acetohydroxamic acid 在 polyphosphoric acid 作用下， 反应 5.0h， 以24%的产率得到6-甲基-2H-1,4-苯并噁嗪-3(4H)-酮
  参考文献：
  名称：

  N-羟基-2-苯氧基乙酰胺和3-苯氧基丙酰胺的分子内环化

  摘要：

  摘要讨论了通过PPA和路易斯酸对N-羟基2-苯氧基乙酰胺和N-羟基-3苯氧基丙酰胺进行分子内环化反应制备2H-1,4-苯并恶嗪-3（4H）酮和1,5苯并x庚酮的新途径。 图形概要 使用PPA和路易斯酸，通过N-羟基2-苯氧基乙酰胺和N-羟基-3苯氧基丙酰胺及其乙酰基和苯甲酰基衍生物的亲电芳族取代反应制备2H-1,4-苯并恶嗪-3（4H）酮和1,5-苯并a嗪酮。

  DOI：

  10.1007/s12039-020-01769-2
• 作为产物：
  描述：

  乙酸-(4-甲基苯氧基)乙酯 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以62%的产率得到2-(p-methylphenoxy)acetohydroxamic acid
  参考文献：
  名称：

  The synthesis and evaluation of phenoxyacylhydroxamic acids as potential agents for Helicobacter pylori infections

  摘要：

  Two series of omega-phenoxy contained acylhydroxamic acids as novel urease inhibitors were designed and synthesized. Biological activity evaluations revealed that co-phenoxypropinoylhydroxamic acids were more active than phenoxyacetohydroxamic acids. Out of these compounds, 3-(3,4-dichlorophenoxy)propionylhydroxamic acid c24 showed significant potency against urease in both cell free extract (IC50 = 0.061 +/- 0.003 mu M) and intact cell (IC50 = 0.89 +/- 0.05 mu M), being over 450- and 120-fold more potent than the clinically prescribed urease inhibitor AHA, repectively. Non-linear fitting of experimental data (V-[S]) suggested a mixed-type inhibition mechanism and a dual site binding mode of these compounds.

  DOI：

  10.1016/j.bmc.2018.07.003

文献信息

• Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene
  作者：Qianshou Zong、Tianwen Bai、Guanyinsheng Qiu、Ming Hou、Zhide Zhang、Xiaojing Lai、Miaofeng Ren

  DOI：10.1055/a-2183-0262

  日期：2024.2

  in 1,4-dioxane is reported for the synthesis of biologically interesting benzoxazin-3(4H)-ones. It is believed that irradiation with a blue LED facilitates the reaction, serving as a source of energy. The SEAr reaction pathway is ascribed to the electronic effects present in the aryl ring of the substrates. The reaction is also applicable for the synthesis of useful scaffolds possessing a quinolin-2-one

  据报道，在 1,4-二恶烷中使用 FeCl3 对 N-酰氧基酰胺进行光诱导分子内亲电芳香取代 (SEAr)，用于合成具有生物学意义的苯并恶嗪-3(4H)-酮。据信，蓝色 LED 的照射会促进反应，从而充当能量来源。SEAr 反应途径归因于底物芳环中存在的电子效应。该反应还适用于合成具有喹啉-2-一核心的有用支架，例如抗癌试剂以及布西哌唑和西洛酰胺的类似物。
• Eckstein; Urbanski, Przemysl Chemiczny, 1956, vol. 35, p. 640
  作者：Eckstein、Urbanski

  DOI：——

  日期：——
• Eckstein; Urbanski, Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1956, vol. <III> 4, p. 627,628
  作者：Eckstein、Urbanski

  DOI：——

  日期：——
• COMPOSITION AND METHODS FOR THE DESIGN AND DEVELOPMENT OF METALLO-ENZYME INHIBITORS
  申请人：Pellecchia Maurizio

  公开号：US20100041653A1

  公开（公告）日：2010-02-18

  The present disclosure provides compounds having the general structure A or pharmaceutically acceptable salts thereof: R—X  (A) wherein R is an alkyl or aryl moiety comprising heterocyclic structures; and X is a metal-chelatin group selected from: This disclosure further provides a focused library of compounds for use in the discovery and design of metallo-enzyme inhibitors. This fragment-based approach provides an assembly of a library of low molecular weight compounds (MW<300 Da) containing a variety of potential metal-chelating groups. The identification of the inhibitory scaffolds among these compounds provides the initial hit fragments that may be optimized for affinity against a particular target using common medicinal chemistry, structure-based or NMR-based approaches.
• CN115707691
  申请人：——

  公开号：——

  公开（公告）日：——