dimethyl (4-(4-(((5-(dimethylamino)naphthalene)-1-sulfonamido)methyl)-1H-1,2,3-triazol-1-yl)butyl)phosphonate | 1219451-26-9

• 英文名称: dimethyl (4-(4-(((5-(dimethylamino)naphthalene)-1-sulfonamido)methyl)-1H-1,2,3-triazol-1-yl)butyl)phosphonate
• CAS: 1219451-26-9
• 化学式: C₂₁H₃₀N₅O₅PS
• 分子量: 495.539
• InChiKey: BAPZUTLASVPVEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  115.65
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  dimethyl (4-(4-(((5-(dimethylamino)naphthalene)-1-sulfonamido)methyl)-1H-1,2,3-triazol-1-yl)butyl)phosphonate 在 水 、 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  Inhibition of acetylcholinesterase by chromophore-linked fluorophosphonates

  摘要：

  Fluorophosphonate (FP) head groups were tethered to a variety of chromophores (C) via a triazole group and tested as FPC inhibitors of recombinant mouse (rMoAChE) and electric eel (EEAChE) acetylcholinesterase. The inhibitors showed bimolecular inhibition constants (k(i)) ranging from 0.3 x 10(5) M-1 min(1) to 10.4 x 10(5) M-1 min(1). When tested against rMoAChE, the dansyl FPC was 12.5-fold more potent than the corresponding inhibitor bearing a Texas Red as chromophore, whereas the Lissamine and dabsyl chromophores led to better anti-EEAChE inhibitors. Most inhibitors were equal or better inhibitors of rMoAChE than EEAChE. 3-Azidopropylfluorophosphonate, which served as one of the FP head groups, showed excellent inhibitory potency against both AChE's (congruent to 1 x 10(7) M-1 min(1)) indicating, in general, that addition of the chromophore reduced the overall anti-AChE activity. Covalent attachment of the dabsyl-FPC analog to rMoAChE was demonstrated using size exclusion chromatography and spectroscopic analysis, and visualized using molecular modeling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.007
• 作为产物：
  描述：

  dimethyl 4-azidobutylphosphonate 、 5-(dimethylamino)-N-(prop-2-yn-1-yl)naphthalene-1-sulfonamide 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 生成 dimethyl (4-(4-(((5-(dimethylamino)naphthalene)-1-sulfonamido)methyl)-1H-1,2,3-triazol-1-yl)butyl)phosphonate
  参考文献：
  名称：

  Inhibition of acetylcholinesterase by chromophore-linked fluorophosphonates

  摘要：

  Fluorophosphonate (FP) head groups were tethered to a variety of chromophores (C) via a triazole group and tested as FPC inhibitors of recombinant mouse (rMoAChE) and electric eel (EEAChE) acetylcholinesterase. The inhibitors showed bimolecular inhibition constants (k(i)) ranging from 0.3 x 10(5) M-1 min(1) to 10.4 x 10(5) M-1 min(1). When tested against rMoAChE, the dansyl FPC was 12.5-fold more potent than the corresponding inhibitor bearing a Texas Red as chromophore, whereas the Lissamine and dabsyl chromophores led to better anti-EEAChE inhibitors. Most inhibitors were equal or better inhibitors of rMoAChE than EEAChE. 3-Azidopropylfluorophosphonate, which served as one of the FP head groups, showed excellent inhibitory potency against both AChE's (congruent to 1 x 10(7) M-1 min(1)) indicating, in general, that addition of the chromophore reduced the overall anti-AChE activity. Covalent attachment of the dabsyl-FPC analog to rMoAChE was demonstrated using size exclusion chromatography and spectroscopic analysis, and visualized using molecular modeling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.007