2-acetamido-3-(benzo[d]thiazol-2-yldisulfaneyl)-N-butyl-3-methylbutanamide | 1430810-95-9

• 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
• 英文名称: 2-acetamido-3-(benzo[d]thiazol-2-yldisulfaneyl)-N-butyl-3-methylbutanamide
• CAS: 1430810-95-9
• 化学式: C₁₈H₂₅N₃O₂S₃
• 分子量: 411.613
• InChiKey: OQXFCTDRFKYKOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3-(benzo[d]thiazol-2-yldisulfaneyl)-N-butyl-3-methylbutanamide 、 二苯基硫代乙酸 以 氯仿 为溶剂， 反应 0.17h， 生成 SS-(3-acetamido-4-(butylamino)-2-methyl-4-oxobutan-2-yl) 2,2-diphenylethane(dithioperoxoate)
  参考文献：
  名称：

  Controllable Hydrogen Sulfide Donors and Their Activity against Myocardial Ischemia-Reperfusion Injury

  摘要：

  Hydrogen sulfide (H2S), known as an important cellular signaling molecule, plays critical roles in many physiological and/or pathological processes. Modulation of H2S levels could have tremendous therapeutic value. However, the study on H2S has been hindered due to the lack of controllable H2S releasing agents that could mimic the slow and moderate H2S release in vivo. In this work we report the design, synthesis, and biological evaluation of a new class of controllable H2S donors. Twenty-five donors were prepared and tested. Their structures were based on a perthiol template, which was suggested to be involved in H2S biosynthesis. H2S release mechanism from these donors was studied and proved to be thiol-dependent. We also developed a series of cell based assays to access their H2S-related activities. H9c2 cardiac rnyocytes were used M these experiments. We tested lead donors cytotoxicity and confirmed their H2S production in cells. Finally we demonstrated that selected donors showed potent protective effects in an in vivo murine model of myocardial ischemia-reperfuSion injury, through a H2S-related mechanism.

  DOI：

  10.1021/cb400090d
• 作为产物：
  描述：

  2-acetamido-N-butyl-3-mercapto-3-methylbutanamide 、 二硫化二苯并噻唑 以 氯仿 为溶剂， 反应 48.0h， 生成 2-acetamido-3-(benzo[d]thiazol-2-yldisulfaneyl)-N-butyl-3-methylbutanamide
  参考文献：
  名称：

  Controllable Hydrogen Sulfide Donors and Their Activity against Myocardial Ischemia-Reperfusion Injury

  摘要：

  Hydrogen sulfide (H2S), known as an important cellular signaling molecule, plays critical roles in many physiological and/or pathological processes. Modulation of H2S levels could have tremendous therapeutic value. However, the study on H2S has been hindered due to the lack of controllable H2S releasing agents that could mimic the slow and moderate H2S release in vivo. In this work we report the design, synthesis, and biological evaluation of a new class of controllable H2S donors. Twenty-five donors were prepared and tested. Their structures were based on a perthiol template, which was suggested to be involved in H2S biosynthesis. H2S release mechanism from these donors was studied and proved to be thiol-dependent. We also developed a series of cell based assays to access their H2S-related activities. H9c2 cardiac rnyocytes were used M these experiments. We tested lead donors cytotoxicity and confirmed their H2S production in cells. Finally we demonstrated that selected donors showed potent protective effects in an in vivo murine model of myocardial ischemia-reperfuSion injury, through a H2S-related mechanism.

  DOI：

  10.1021/cb400090d

文献信息

• 9-Fluorenylmethyl (Fm) Disulfides: Biomimetic Precursors for Persulfides
  作者：Chung-Min Park、Brett A. Johnson、Jicheng Duan、Jeong-Jin Park、Jacob J. Day、David Gang、Wei-Jun Qian、Ming Xian

  DOI：10.1021/acs.orglett.5b03557

  日期：2016.3.4

  thiols (−SH) to form −S-SFm adducts under mild conditions. This method allows for a H2S-free and biomimetic protocol to generate highly reactive persulfides (in their anionic forms). The high nucleophilicity of persulfides toward a number of thiol-blocking reagents is also demonstrated. The method holds promise for further understanding the chemical biology of persulfides and S-sulfhydration.

  报道了功能性二硫键FmSSPy-A（Fm = 9-芴基甲基； Py =吡啶基）的形成。它可以在温和条件下有效地将小分子和蛋白质硫醇（-SH）转化为-S-SFm加合物。该方法可实现无H 2 S仿生实验，以生成高反应性的过硫化物（呈阴离子形式）。还证明了过硫化物对多种硫醇封闭剂的高度亲核性。该方法为进一步理解过硫化物和S-硫氢化的化学生物学提供了希望。