3-(benzo[d]thiazol-2-yl)-7-mercapto-2H-chromen-2-one | 1356543-39-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(benzo[d]thiazol-2-yl)-7-mercapto-2H-chromen-2-one
• 英文别名: 3-(1,3-benzothiazol-2-yl)-7-sulfanylchromen-2-one
• CAS: 1356543-39-9
• 化学式: C₁₆H₉NO₂S₂
• 分子量: 311.385
• InChiKey: BQZSRFNCHMNINF-UHFFFAOYSA-N

物化性质

• 沸点：
  549.4±60.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(benzo[d]thiazol-2-yl)-7-mercapto-2H-chromen-2-one 在 T406石油添加剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-(benzo[d]thiazol-2-yl)-7-(benzyldisulfanyl)-2H-chromen-2-one
  参考文献：
  名称：

  Fluorescent Coumarin Thiols Measure Biological Redox Couples

  摘要：

  In this report we present a new chemical probe, 3-HTC, that can reversibly and ratiometrically measure the thiol-disulfide equilibrium of biological systems. 3-HTC is composed of a coumarin that has a thiolate directly conjugated to its extended aromatic pi system while formation of a disulfide attenuates this conjugation. The fluorescence and absorption properties of 3-HTC are therefore very sensitive to the redox state of its thiol. 3-HTC reacts reversibly with thiols and disulfides enabling its use to measure dynamic GSH/GSSH ratios in vitro as well as to monitor the reversible redox status of whole cell lysates.

  DOI：

  10.1021/ol203105c
• 作为产物：
  描述：

  3-(benzo[d]thiazol-2-yl)-2-imino-2H-chromene-7-thiol 在 盐酸 、 水 作用下， 反应 18.0h， 生成 3-(benzo[d]thiazol-2-yl)-7-mercapto-2H-chromen-2-one
  参考文献：
  名称：

  Fluorescent Coumarin Thiols Measure Biological Redox Couples

  摘要：

  In this report we present a new chemical probe, 3-HTC, that can reversibly and ratiometrically measure the thiol-disulfide equilibrium of biological systems. 3-HTC is composed of a coumarin that has a thiolate directly conjugated to its extended aromatic pi system while formation of a disulfide attenuates this conjugation. The fluorescence and absorption properties of 3-HTC are therefore very sensitive to the redox state of its thiol. 3-HTC reacts reversibly with thiols and disulfides enabling its use to measure dynamic GSH/GSSH ratios in vitro as well as to monitor the reversible redox status of whole cell lysates.

  DOI：

  10.1021/ol203105c