5-(二甲氨基)-N-(4-羟基丁基)萘-1-磺酰胺 | 110232-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-(二甲氨基)-N-(4-羟基丁基)萘-1-磺酰胺
• 英文名称: 1-Naphthalenesulfonamide, 5-(dimethylamino)-N-(4-hydroxybutyl)-
• 英文别名: 5-(dimethylamino)-N-(4-hydroxybutyl)naphthalene-1-sulfonamide
• CAS: 110232-20-7
• 化学式: C₁₆H₂₂N₂O₃S
• 分子量: 322.428
• InChiKey: RHUAFMOLUNAWRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  505.8±60.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(二甲氨基)-N-(4-羟基丁基)萘-1-磺酰胺 在 重铬酸吡啶 、 亚硝酸 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 13.5h， 生成 5-(dimethylamino)-N-(4-nitrososulfanylpentyl)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：

  4-氨基-1-丁醇 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到5-(二甲氨基)-N-(4-羟基丁基)萘-1-磺酰胺
  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

文献信息

• Synthesis of novel fluorescently labeled sphingomyelin derivatives useful for sphingomyelinase assay
  作者：John J. Gaudino、Kirsten Bjergarde、Po-Ying Chan-Hui、Clifford D. Wright、David S. Thomson

  DOI：10.1016/s0960-894x(97)00184-4

  日期：1997.5

  Substrates for the sphingomyelinase enzyme class have been prepared, which contain a fluorescent tag and a biotin moiety. These molecules are useful for development of rapid high throughput assays for sphingomyelinase activity. It was observed that retaining the choline ammonium group (as found in the native sphingomyelinase substrate) in synthetic substrates was critical to retain high cleavage rate by the enzyme. (C) 1997 Elsevier Science Ltd.
• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  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.