N-(2-phenoxyphenyl)-7-[4-(3-pyridinyl)-1H-1,2,3-triazol-1-yl]heptanamide | 1202580-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-phenoxyphenyl)-7-[4-(3-pyridinyl)-1H-1,2,3-triazol-1-yl]heptanamide
• 英文别名: N-(2-phenoxyphenyl)-7-(4-pyridin-3-yltriazol-1-yl)heptanamide
• CAS: 1202580-67-3
• 化学式: C₂₆H₂₇N₅O₂
• 分子量: 441.533
• InChiKey: BOWRJMOJYLNMFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-乙炔基吡啶 、 7-azido-N-(2-phenoxyphenyl)heptanamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以78%的产率得到N-(2-phenoxyphenyl)-7-[4-(3-pyridinyl)-1H-1,2,3-triazol-1-yl]heptanamide
  参考文献：
  名称：

  A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry

  摘要：

  The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited copper-catalyzed [3 + 2] cycloaddition between azides and alkynes (click chemistry) to synthesize 185 novel analogues. The most promising compound displays an IC50 for cytotoxicity in vitro of 3.8 +/- 0.3 nM and an IC50 for NAD depletion of 3.0 +/- 0.4 nM. Herein, we strengthen previous data suggesting that this class of compounds induces autophagic cell death. In addition to characterizing this compound and providing a rationale via molecular docking, we reinforce the excellent potential of click chemistry for rapidly generating structure-activity relationships and for drug screening.

  DOI：

  10.1021/jm9010669

文献信息

• A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry
  作者：Giampiero Colombano、Cristina Travelli、Ubaldina Galli、Antonio Caldarelli、Maria Giovanna Chini、Pier Luigi Canonico、Giovanni Sorba、Giuseppe Bifulco、Gian Cesare Tron、Armando A. Genazzani

  DOI：10.1021/jm9010669

  日期：2010.1.28

  The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited copper-catalyzed [3 + 2] cycloaddition between azides and alkynes (click chemistry) to synthesize 185 novel analogues. The most promising compound displays an IC50 for cytotoxicity in vitro of 3.8 +/- 0.3 nM and an IC50 for NAD depletion of 3.0 +/- 0.4 nM. Herein, we strengthen previous data suggesting that this class of compounds induces autophagic cell death. In addition to characterizing this compound and providing a rationale via molecular docking, we reinforce the excellent potential of click chemistry for rapidly generating structure-activity relationships and for drug screening.