5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinannyl-2-disulfanyl-2-propene | 1208093-46-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机二硫代磷酸及其衍生物
• 英文名称: 5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinannyl-2-disulfanyl-2-propene
• CAS: 1208093-46-2
• 化学式: C₈H₁₅O₂PS₃
• 分子量: 270.378
• InChiKey: ZVIAXDXCZSKBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinannyl-2-disulfanyl-2-propene 、 D-cysteine 在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 S-allylmercaptocysteine
  参考文献：
  名称：

  S-Alk(en)ylmercaptocysteine: Chemical Synthesis, Biological Activities, and Redox-Related Mechanism

  摘要：

  S-Alk(en)ylmercaptocysteine (CySSR, R = methyl, ethyl, propyl, 1-propenyl, and ally!), which are the putative metabolites of Allium thiosulfinates, were chemically synthesized. CySSR, but not the corresponding monosulfide species S-alk(en)yl cysteine (CySR), were able to induce quinone reductase (QR, a representative phase II enzyme) in Hepa 1c1c7 cells and inhibit nitric oxide (NO, an inflammatory biomarker) formation in lipopolysaccharide (LPS)-activated RAW 264.7 cells. These results indicate the importance of the disulfide bond for the biological activities of CySSR. Glutathione (GSH) and N-acetylcysteine (NAC), but not other types of cellular antioxidants, suppressed multiple biological activities of CySSR in vitro. The inhibitory effects of GSH and NAC on the biological activities of CySSR were correlated with a glutaredoxin (Grx)-dependent intracellular reduction of CySSR to generate cysteine and RSH, which were secreted into the extracellular medium.

  DOI：

  10.1021/jf305486q
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 tetraphosphorus decasulfide 、 溴 、 碘 、 potassium iodide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinannyl-2-disulfanyl-2-propene
  参考文献：
  名称：

  S-Alk(en)ylmercaptocysteine: Chemical Synthesis, Biological Activities, and Redox-Related Mechanism

  摘要：

  S-Alk(en)ylmercaptocysteine (CySSR, R = methyl, ethyl, propyl, 1-propenyl, and ally!), which are the putative metabolites of Allium thiosulfinates, were chemically synthesized. CySSR, but not the corresponding monosulfide species S-alk(en)yl cysteine (CySR), were able to induce quinone reductase (QR, a representative phase II enzyme) in Hepa 1c1c7 cells and inhibit nitric oxide (NO, an inflammatory biomarker) formation in lipopolysaccharide (LPS)-activated RAW 264.7 cells. These results indicate the importance of the disulfide bond for the biological activities of CySSR. Glutathione (GSH) and N-acetylcysteine (NAC), but not other types of cellular antioxidants, suppressed multiple biological activities of CySSR in vitro. The inhibitory effects of GSH and NAC on the biological activities of CySSR were correlated with a glutaredoxin (Grx)-dependent intracellular reduction of CySSR to generate cysteine and RSH, which were secreted into the extracellular medium.

  DOI：

  10.1021/jf305486q

文献信息

• Cysteine and Glutathione Mixed-Disulfide Conjugates of Thiosulfinates: Chemical Synthesis and Biological Activities
  作者：Guodong Zhang、Bin Li、Chen-Hsien Lee、Kirk L. Parkin

  DOI：10.1021/jf9029354

  日期：2010.2.10

  The chemical syntheses of cysteine (CYS) and glutathione (GSH) mixed -disulfide conjugates (CySSR, GSSR, respectively) of mercapto residues representing most of the R groups of thiosulfinates (R = methyl, ethyl, propyl, and allyl) are described. Gram-scale conjugates were prepared as >98% pure preparations, with 80% reaction yield for each of the two seminal synthesis steps, with structures confirmed by H-1 NMR and high-resolution MS analyses. These conjugates are derivatives of thiosulfinates that may be evolved in processed foods, in the digestive tract, and through in vivo metabolism. The prepared conjugates were found to be able to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7), indicating they have potential cancer preventive and anti-inflammatory activities. Among the prepared conjugates, the allyl conjugates of CYS and GSH, S-allylmercaptocysteine (CySSA) and S-allylmercaptoglutathione (GSSA), showed the most potent activity regarding QR induction and NO production inhibition. The conjugates with saturated R groups were also active and conferred biological activity as cystine and oxidized glutathione exhibited no effects in these cellular assays.