N-(3-Acetylthiopropyl)-5-dimethylaminonaphthalene-1-sulfonamide | 195058-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-Acetylthiopropyl)-5-dimethylaminonaphthalene-1-sulfonamide
• 英文别名: S-[3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]propyl] ethanethioate
• CAS: 195058-01-6
• 化学式: C₁₇H₂₂N₂O₃S₂
• 分子量: 366.505
• InChiKey: RWWGDWOYVFJEIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3-Acetylthiopropyl)-5-dimethylaminonaphthalene-1-sulfonamide 在 air 、 sodium methylate 作用下， 生成 N,N'-(4,5-Dithiaoctane-1,8-diyl)bis(5-dimethylaminonaphthalene-1-sulfonamide)
  参考文献：
  名称：

  Direct C-11 functionalisation of anatoxin-a. Application to the synthesis of new ligand-based structural probes

  摘要：

  评估了多种对锐毒毒素-a 的 C-11 甲基进行官能化的方法。N-Boc 锐毒毒素-a 9 与 PhI(OH)OTs（科塞试剂）的反应是首选方法，可得到合成用途广泛的 α-甲氧基酮 10。这种中间体为通过硫醚连接将间隔单元连接到 C-11 提供了方便的载体，已被用于合成丹酰化的[N-（5-二甲基氨基-1-萘磺酰基）]锐毒毒素-a 衍生物。此外，还报告了与α-硫代甲基锐毒毒素-a 衍生物 16 以及丹酰化配体 25 和 26 有关的初步生物数据。

  DOI：

  10.1039/a702087b
• 作为产物：
  描述：

  5-dimethylamino-naphthalene-1-sulfonic acid (3-hydroxy-propyl)-amide 在 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 N-(3-Acetylthiopropyl)-5-dimethylaminonaphthalene-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

文献信息

• 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.
• Direct C-11 functionalisation of anatoxin-a. Application to the synthesis of new ligand-based structural probes
  作者：Nicholas A. Magnus、Laurent Ducry、Valérie Rolland、Susan Wonnacott、Timothy Gallagher

  DOI：10.1039/a702087b

  日期：——

  A variety of methods have been evaluated for the functionalisation of the C-11 methyl group of anatoxin-a. Reaction of N-Boc anatoxin-a 9 with PhI(OH)OTs (Koser’s reagent) represents the method of choice and gives the synthetically versatile α-tosyloxy ketone 10. This intermediate provides a convenient vehicle for the attachment of spacer units to C-11 via a thioether linkage which has been applied to the synthesis of the dansylated [N-(5-dimethylamino-1-naphthylsulfonyl)] anatoxin-a derivatives. Preliminary biological data relating to the α-thiomethyl anatoxin-a derivative 16 and the dansylated ligands, 25 and 26, are also reported.

  评估了多种对锐毒毒素-a 的 C-11 甲基进行官能化的方法。N-Boc 锐毒毒素-a 9 与 PhI(OH)OTs（科塞试剂）的反应是首选方法，可得到合成用途广泛的 α-甲氧基酮 10。这种中间体为通过硫醚连接将间隔单元连接到 C-11 提供了方便的载体，已被用于合成丹酰化的[N-（5-二甲基氨基-1-萘磺酰基）]锐毒毒素-a 衍生物。此外，还报告了与α-硫代甲基锐毒毒素-a 衍生物 16 以及丹酰化配体 25 和 26 有关的初步生物数据。