2,2'-dithiobispyrazine | 98437-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,2'-dithiobispyrazine
• 英文别名: 2,2'-disulfanediyl-bis-pyrazine；Bis--disulfid；2-(Pyrazin-2-yldisulfanyl)pyrazine
• CAS: 98437-14-0
• 化学式: C₈H₆N₄S₂
• 分子量: 222.294
• InChiKey: GBQYJGUYRJBIRI-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C(Solv: methanol (67-56-1); ligroine (8032-32-4))
• 沸点：
  374.7±37.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-巯基吡嗪 在 sodium hydroxide 、 碘 、 potassium iodide 作用下， 以 sodium hydroxide 、 水 为溶剂， 反应 3.0h， 以0.3 g的产率得到2,2'-dithiobispyrazine
  参考文献：
  名称：

  Inhibition of lipopolysaccharide-induced inducible nitric oxide synthase expression by a novel compound, mercaptopyrazine, through suppression of nuclear factor-kappaB binding to DNA

  摘要：

  Macrophage cells in response to cytokines and endotoxins produced a large amount of nitric oxide (NO) by expression of inducible nitric oxide synthase (iNOS), resulting in acute or chronic inflammatory disorders including septic hypotension and atherosclerosis. In the present study, we investigated the effect and the mechanism of mercaptopyrazine (MP) in the induction of iNOS and NO production as a culminating factor for several inflammatory disorders. Pretreatment of MP alleviated the mortality of endotoxemic mice receiving a lethal bolus of lipopolysaccharide (LPS), which was associated with the reduced levels of serum nitrite/nitrate and IL-1beta. In RAW264.7 mouse macrophage cells, MP (300 muM) inhibited both protein and mRNA levels of iNOS stimulated by LPS/interferon-gamma (IFNgamma) up to 50%. The nuclear factor-kappa B (NF-kappaB)-driven transactivation was also suppressed by MP to the same degree. Treatment of MP reduced the binding of NF-kappaB to the oligonucleotides containing NF-kappaB consensus sequence, while it did not affect the translocation of NF-kappaB to nuclear. Suppression of NF-kappaB activity by MP was completely reversed by a reducing agent, dithiothreitol, implying that MP might oxidize the sulfhydryl group(s) of DNA binding domain of NF-kappaB. In conclusion, MP would be one of interesting candidates or chemical moieties of iNOS expression inhibitor via specific suppression of NF-kappaB binding to DNA, and be useful as a chemopreventive agent or a therapeutic against iNOS-associated inflammatory diseases. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2004.05.005

文献信息

• US3937718A
  申请人：——

  公开号：US3937718A

  公开（公告）日：1976-02-10