5-Dimethylamino-naphthalene-1-sulfonic acid (6-mercapto-hexyl)-amide | 1026124-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Dimethylamino-naphthalene-1-sulfonic acid (6-mercapto-hexyl)-amide
• 英文别名: 5-(dimethylamino)-N-(6-sulfanylhexyl)naphthalene-1-sulfonamide
• CAS: 1026124-09-3
• 化学式: C₁₈H₂₆N₂O₂S₂
• 分子量: 366.549
• InChiKey: YWWHKHZGFKAZGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Dimethylamino-naphthalene-1-sulfonic acid (6-mercapto-hexyl)-amide 在 亚硝酸 作用下， 以 甲醇 、 水 为溶剂， 生成 5-(dimethylamino)-N-(6-nitrososulfanylhexyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  6-氨基-1-己醇 在 二异丁基氢化铝 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 生成 5-Dimethylamino-naphthalene-1-sulfonic acid (6-mercapto-hexyl)-amide
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p