14-(p-chlorophenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile | 1438434-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 14-(p-chlorophenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile
• CAS: 1438434-67-3
• 化学式: C₂₄H₁₄ClN₅O
• 分子量: 423.861
• InChiKey: FRIGNHPJAOCVID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.1
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  14-(p-chlorophenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile 在 盐酸羟胺 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以70%的产率得到2-(14-(4-chlorophenyl)-14H-naphto[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)acetamidoxime
  参考文献：
  名称：

  Design, synthesis of novel pyranotriazolopyrimidines and evaluation of their anti-soybean lipoxygenase, anti-xanthine oxidase, and cytotoxic activities

  摘要：

  The synthesis of 14-(aryl)-14H-naphto[2,1-b] pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-yl) acetamidoximes 2a-e has been accomplished by reaction of 2-acetonitrile derivatives 1a-e with hydroxylamine. Cyclocondensation reaction of precursors 2a-e with some elctrophilic species such as ethylorthoformate, acetic anhydride, and methyl-acetoacetate provided the new oxadiazole derivatives 3a-e, 4a-e, and 5a-e, respectively. On the other hand, the reaction of precursors 2a-e with 2-chloropropanoyl chloride afforded the new acetimidamides 6a-e which evolve under reflux of toluene to the new oxadiazoles 7a-e. The synthetic compounds were screened for their anti-xanthine oxidase, anti-soybean lipoxygenase, and cytotoxic activities. Moderate to weak xanthine oxidase and soybean lipoxygenase inhibitions were obtained but significant cytotoxic activities were noted. The most cytotoxic activities were recorded mainly (i) 5a was the most active (IC50 = 4.0 mu M) and selective against MCF-7 and (ii) 2a was cytotoxic against the four cell lines with selectivity for MCF-7 and OVCAR-3 (IC50 = 17 and 12 mu M, respectively) while 2e is highly selective against OVCAR-3 (IC50 = 10 mu M).

  DOI：

  10.3109/14756366.2015.1118684
• 作为产物：
  描述：

  4-氯苯甲醛 在 乙酸酐 、 sodium carbonate 、 溶剂黄146 、 肼 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 14-(p-chlorophenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile
  参考文献：
  名称：

  Synthesis of Novel Fused Coumarine and naphtho[2,1-b]pyrano[3,2- e][1,2,4] triazolo[1,5-c]pyrimidine Derivatives

  摘要：

  制备了新的14-(芳基)-14H-萘基[2,1-b]吡喃并[3,2-e][1,2,4]三唑并[1,5-c]嘧啶-2-乙腈。 研究了这些化合物与水杨醛的 Knoevenagel 缩合的化学行为 衍生物，因此，一系列 2-(香豆素-3''-基)-14(芳基)-14H-萘基[2,1-b]吡喃并[3,2-e][1,2,4]三唑并[1,5- 获得c]嘧啶。通过IR、ES-HR-MS、1H NMR和13C NMR对其结构进行了表征。

  DOI：

  10.2174/1570178611310030007