S-(4-fluorobenzoyl)thiohydroxylamine | 1571113-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-(4-fluorobenzoyl)thiohydroxylamine
• CAS: 1571113-48-8
• 化学式: C₇H₆FNOS
• 分子量: 171.195
• InChiKey: XQOGDBCFBOOLKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-(4-fluorobenzoyl)thiohydroxylamine 、 苯甲酸酐 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 S-benzamido 4-fluorobenzenecarbothioate
  参考文献：
  名称：

  Design, Synthesis, and Cardioprotective Effects of N-Mercapto-Based Hydrogen Sulfide Donors

  摘要：

  Hydrogen sulfide (H2S) is a signaling molecule which plays regulatory roles in many physiological and/or pathological processes. Therefore, regulation of H2S levels could have great potential therapeutic value. In this work, we report the design, synthesis, and evaluation of a class of N-mercapto (N-SH)-based H2S donors. Thirty-three donors were synthesized and tested. Our results indicated that controllable H2S release from these donors could be achieved upon structural modifications. Selected donors (NSHD-1, NSHD-2, and NSHD-6) were tested in cellular models of oxidative damage and showed significant cytoprotective effects. Moreover, NSHD-1 and NSHD-2 were also found to exhibit potent protective effects in a murine model of myocardial ischemia reperfusion (MI/R) injury.

  DOI：

  10.1021/acs.jmedchem.5b01033
• 作为产物：
  描述：

  4-fluorobenzothioic S-acid 在 potassium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 水 为溶剂， 反应 0.08h， 生成 S-(4-fluorobenzoyl)thiohydroxylamine
  参考文献：
  名称：

  Design, Synthesis, and Cardioprotective Effects of N-Mercapto-Based Hydrogen Sulfide Donors

  摘要：

  Hydrogen sulfide (H2S) is a signaling molecule which plays regulatory roles in many physiological and/or pathological processes. Therefore, regulation of H2S levels could have great potential therapeutic value. In this work, we report the design, synthesis, and evaluation of a class of N-mercapto (N-SH)-based H2S donors. Thirty-three donors were synthesized and tested. Our results indicated that controllable H2S release from these donors could be achieved upon structural modifications. Selected donors (NSHD-1, NSHD-2, and NSHD-6) were tested in cellular models of oxidative damage and showed significant cytoprotective effects. Moreover, NSHD-1 and NSHD-2 were also found to exhibit potent protective effects in a murine model of myocardial ischemia reperfusion (MI/R) injury.

  DOI：

  10.1021/acs.jmedchem.5b01033

文献信息

• <i>S</i>-Aroylthiooximes: A Facile Route to Hydrogen Sulfide Releasing Compounds with Structure-Dependent Release Kinetics
  作者：Jeffrey C. Foster、Chadwick R. Powell、Scott C. Radzinski、John B. Matson

  DOI：10.1021/ol500385a

  日期：2014.3.21

  We report the facile preparation of a family of S-aroylthiooxime (SATO) H2S donors, which are synthesized via a click reaction analogous to oxime formation between S-aroylthiohydroxylamines (SATHAs) and aldehydes or ketones. Analysis of cysteine-triggered H2S release revealed structure-dependent release kinetics with half-lives from 8–82 min by substitution of the SATHA ring. The pseudo-first-order

  我们报告的家庭-S-芳香酰硫肟（SATO）H 2 S供体的简便制备，通过类似于在S-芳香酰硫羟胺（SATHAs）与醛或酮之间肟形成的点击反应合成。半胱氨酸触发的H 2 S释放分析表明，通过取代SATHA环，结构依赖的释放动力学具有8-82分钟的半衰期。取代的SATO的拟一阶速率常数符合标准线性自由能关系（ρ= 1.05），表明对电子效应具有显着的敏感性。
• Supramolecular Tuning of H₂S Release from Aromatic Peptide Amphiphile Gels: Effect of Core Unit Substituents
  作者：Yun Qian、Kuljeet Kaur、Jeffrey C. Foster、John B. Matson

  DOI：10.1021/acs.biomac.8b01732

  日期：2019.2.11

  substituents on the SATO group affected H2S release rates predictably in line with electronic effects (Hammett σ values) according to a linear free energy relationship. Above the CAC, circular dichroism, infrared, and fluorescence spectroscopies demonstrated that substituents influenced the self-assembled structures by affecting hydrogen bonding (β-sheet formation) and π-π stacking. At these concentrations, electronic

  H2S是一种具有多种生理作用的气体递质，但是其反应性和在生物介质中的半衰期短，使其难以控制地传递。对于气体的生物应用，水凝胶具有传递 的潜力，与其他供体系统相比具有许多优势，包括局部传递，控制释放速率，生物降解和可变的机械性能。在这项研究中，我们设计和评估了可控的 输送的基于肽的 释放水凝胶。这些水凝胶是由短的，自组装的芳香族肽两亲物（APA）制备的，在其N端被S-芳基硫代肟（SATO）官能化，后者会响应硫醇触发而释放 。研究了APA的溶液形式和凝胶形式，并通过添加CAChref=https://www.molaid.com/MS_35596 target="_blank">CaCl2引发了凝胶作用。APA的SATO组分上包含各种取代基，以评估它们对溶液相和凝胶相中自组装形态和 释放速率的影响。透射电子显微镜（TEM）图像证实，所有释放 的APA均自组装成纳米纤维，高于临界聚集浓度（CAC）约〜0.5 mg / mL。在CAC以下，SATO基团上的取代基根据线性自由能关系，可