S-(4-methoxybenzoyl)thiohydroxylamine | 35124-66-4

• 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-methoxybenzoyl)thiohydroxylamine
• 英文别名: S-Anisoylhydrosulfamin；S-(p-Anisoyl)hydrosulfamin；S-(p-Methoxybenzoyl)thiohydroxylamine；S-amino 4-methoxybenzenecarbothioate
• CAS: 35124-66-4
• 化学式: C₈H₉NO₂S
• 分子量: 183.231
• InChiKey: IDUOPXWIQNWKEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.6±44.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(4-methoxybenzoyl)thiohydroxylamine 在 吡啶 、 高氯酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 2,5-bis(4-methoxyphenyl)-1,3,4-oxathiazol-1-ium;perchlorate
  参考文献：
  名称：

  第一个草根zo鎓阳离子-1,3,4-草根zo鎓盐的简单合成

  摘要：

  1,3,4-氧杂噻唑鎓盐（，）是六种可能的芳族草硫唑鎓阳离子的首批代表，可以很容易地通过将-酰基硫羟胺（）酰化，然后用强酸和苯甲酰环化来制备。酰基酐。与类似的二噻唑鎓盐相比，正电荷似乎离域的程度更小。

  DOI：

  10.1016/s0040-4039(00)97998-x
• 作为产物：
  描述：

  4-methoxythiobenzoic acid 在 potassium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 水 为溶剂， 反应 0.08h， 生成 S-(4-methoxybenzoyl)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H2S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H2S输送的基于肽的H2S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H2S。研究了APA的溶液形式和凝胶形式，并通过添加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H2S释放速率的影响。透射电子显微镜（TEM）图像证实，所有释放H2S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
• YUNG, TOMMY W. K.;SAMMES, MICHAEL P., TETRAHEDRON LETT., 31,(1990) N1, C. 5935-5938
  作者：YUNG, TOMMY W. K.、SAMMES, MICHAEL P.

  DOI：——

  日期：——
• Design, Synthesis, and Cardioprotective Effects of <i>N</i>-Mercapto-Based Hydrogen Sulfide Donors
  作者：Yu Zhao、Chuntao Yang、Chelsea Organ、Zhen Li、Shashi Bhushan、Hiro Otsuka、Armando Pacheco、Jianming Kang、Hector C. Aguilar、David J. Lefer、Ming Xian

  DOI：10.1021/acs.jmedchem.5b01033

  日期：2015.9.24

  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.
• The first oxathiazolium cations - a simple synthesis of 1,3,4-oxathiazolium salts
  作者：Tommy W.K. Yung、Michael P. Sammes

  DOI：10.1016/s0040-4039(00)97998-x

  日期：1990.1

  The 1,3,4-oxathiazolium salts (,), which are the first representatives of the six possible classes of aromatic oxathiazolium cations, are readily prepared by -acylation of the -acylthiohydroxylamines (, ) followed by cyclization with a strong acid and an acyl anhydride. The positive charge appears to be delocalized to a smaller extent than in analogous dithiazolium salts.

  1,3,4-氧杂噻唑鎓盐（，）是六种可能的芳族草硫唑鎓阳离子的首批代表，可以很容易地通过将-酰基硫羟胺（）酰化，然后用强酸和苯甲酰环化来制备。酰基酐。与类似的二噻唑鎓盐相比，正电荷似乎离域的程度更小。

表征谱图