acetic acid 2-hydroxyimino-ethyl ester | 137424-97-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: acetic acid 2-hydroxyimino-ethyl ester
• 英文别名: 2-Acetoxyacetaldoxim；2-(Hydroxyimino)ethyl acetate；2-hydroxyiminoethyl acetate
• CAS: 137424-97-6
• 化学式: C₄H₇NO₃
• 分子量: 117.104
• InChiKey: GFLRGQMBJYFKBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetic acid 2-hydroxyimino-ethyl ester 、 脱氧强的松龙-16-烯 在 benzyltrimethylazanium tetrachloro-λ³-iodanuide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以30%的产率得到(16S,17R)-3′-methylacetate-11β,21-dihydroxy-4′H-pregna-1,4-dieno[16,17-d]isoxazole-3,20-dione
  参考文献：
  名称：

  Discovery of a novel isoxazoline derivative of prednisolone endowed with a robust anti-inflammatory profile and suitable for topical pulmonary administration

  摘要：

  A novel glucocorticoids series of (GCs), 6 alpha,9 alpha-di-Fluoro 3-substituted C-16,17-isoxazolines was designed, synthesised and their structure activity relationship was evaluated with glucocorticoid receptor (GR) binding studies together with GR nuclear translocation cell-based assays. This strategy, coupled with in silica modelling analysis, allowed for the identification of Cpd #15, an isoxazoline showing a sub-nanomolar inhibitory potency (IC50 = 0.84 nM) against TNF alpha-evoked IL-8 release in primary human airways smooth muscle cells. In Raw264.7 mouse macrophages, Cpd #15 inhibited LPS-induced NO release with a potency (IC50 = 6 nM) > 10-fold higher with respect to Dexamethasone. Upon intratracheal (it.) administration, Cpd #15, at 0.1 mu mol/kg significantly inhibited and at 1 mu mol/kg fully counteracted eosinophilic infiltration in a model of allergen-induced pulmonary inflammation in rats. Moreover, Cpd #15 proved to be suitable for pulmonary topical administration given its sustained lung retention (t(1/2) = 6.5 h) and high pulmonary levels (>100-fold higher than plasma levels) upon intratracheal administration in rats. In summary, Cpd #15 displays a pharmacokinetic and pharmacodynamic profile suitable for topical treatment of conditions associated with pulmonary inflammation such as asthma and COPD. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.12.016
• 作为产物：
  描述：

  2-甲基-2-恶唑啉 生成 acetic acid 2-hydroxyimino-ethyl ester
  参考文献：
  名称：

  Peracid oxidation of imino ethers

  摘要：

  DOI：

  10.1021/jo00940a012

文献信息

• Discovery of a novel isoxazoline derivative of prednisolone endowed with a robust anti-inflammatory profile and suitable for topical pulmonary administration
  作者：E. Ghidini、A.M. Capelli、C. Carnini、V. Cenacchi、G. Marchini、A. Virdis、A. Italia、F. Facchinetti

  DOI：10.1016/j.steroids.2014.12.016

  日期：2015.3

  A novel glucocorticoids series of (GCs), 6 alpha,9 alpha-di-Fluoro 3-substituted C-16,17-isoxazolines was designed, synthesised and their structure activity relationship was evaluated with glucocorticoid receptor (GR) binding studies together with GR nuclear translocation cell-based assays. This strategy, coupled with in silica modelling analysis, allowed for the identification of Cpd #15, an isoxazoline showing a sub-nanomolar inhibitory potency (IC50 = 0.84 nM) against TNF alpha-evoked IL-8 release in primary human airways smooth muscle cells. In Raw264.7 mouse macrophages, Cpd #15 inhibited LPS-induced NO release with a potency (IC50 = 6 nM) > 10-fold higher with respect to Dexamethasone. Upon intratracheal (it.) administration, Cpd #15, at 0.1 mu mol/kg significantly inhibited and at 1 mu mol/kg fully counteracted eosinophilic infiltration in a model of allergen-induced pulmonary inflammation in rats. Moreover, Cpd #15 proved to be suitable for pulmonary topical administration given its sustained lung retention (t(1/2) = 6.5 h) and high pulmonary levels (>100-fold higher than plasma levels) upon intratracheal administration in rats. In summary, Cpd #15 displays a pharmacokinetic and pharmacodynamic profile suitable for topical treatment of conditions associated with pulmonary inflammation such as asthma and COPD. (C) 2015 Elsevier Inc. All rights reserved.
• Peracid oxidation of imino ethers
  作者：Donald H. Aue、Darryl Thomas

  DOI：10.1021/jo00940a012

  日期：1974.12