6-(diethylamino)-N-[[1-[3-[fluoro(methoxy)phosphoryl]propyl]triazol-4-yl]methyl]-2-oxochromene-3-carboxamide | 1219451-34-9

• 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: 6-(diethylamino)-N-[[1-[3-[fluoro(methoxy)phosphoryl]propyl]triazol-4-yl]methyl]-2-oxochromene-3-carboxamide
• CAS: 1219451-34-9
• 化学式: C₂₁H₂₇FN₅O₅P
• 分子量: 479.448
• InChiKey: LOANPEJCMDITAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 生成 6-(diethylamino)-N-[[1-[3-[fluoro(methoxy)phosphoryl]propyl]triazol-4-yl]methyl]-2-oxochromene-3-carboxamide
  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