14-(p-methylphenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile | 299401-22-2

• 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-methylphenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile
• 英文别名: 2-(14-(p-tolyl)-14H-benzo[5,6]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)acetonitrile；2-[2-(4-Methylphenyl)-12-oxa-5,7,8,10-tetrazapentacyclo[11.8.0.03,11.04,8.016,21]henicosa-1(13),3(11),4,6,9,14,16,18,20-nonaen-6-yl]acetonitrile
• CAS: 299401-22-2
• 化学式: C₂₅H₁₇N₅O
• 分子量: 403.443
• InChiKey: ZJHVLYMIANXDLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  14-(p-methylphenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-acetonitrile 在 哌啶 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(coumarin-3''-yl)-14-(p-methylphenyl)-14H-naphtho[2,1-b]pyrano[3,2-e][1,2,4]triazolo [1,5-c]pyrimidine
  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
• 作为产物：
  描述：

  3-amino-1-(p-tolyl)-1H-benzo[f]chromene-2-carbonitrile 在 乙酸酐 、 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-methylphenyl)-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

文献信息

• Convenient synthesis and anti-proliferative activity of some benzochromenes and chromenotriazolopyrimidines under classical methods and phase transfer catalysis
  作者：Amira T. Ali、Mohamed H. Hekal

  DOI：10.1080/00397911.2019.1675173

  日期：2019.12.17

  benzotriazolopyrimdine derivatives 3-10 were prepared via reaction of ethyl formimidate 2 with primary amines such as sulfanilamide, cyclohexylamine, 3-aminopyridine, 4-aminoantipyrine in addition to its reactions with different acid hydrazides. Compound 5 was further allowed to react with different C-electrophiles by classical and phase transfer catalysis conditions to get novel chromenotriazolopyrimidine

  摘要 通过甲亚胺酸乙酯2与磺胺、环己胺、3-氨基吡啶、4-氨基安替比林等伯胺反应，并与不同的酰肼反应，制备了一系列新的苯并色烯、苯并并并嘧啶和苯并三唑并嘧啶衍生物3-10。通过经典和相转移催化条件，进一步使化合物5与不同的C-亲电试剂反应，得到新的色并三唑并嘧啶衍生物。针对一组两种人类肿瘤细胞系，即 HepG2 和 HCT-116 细胞系，在体外测试了一些新合成化合物中抗肿瘤活性的筛选。化合物4、7、8、10和20表现出显着的广谱抗肿瘤活性。图形概要
• Design, synthesis of novel pyranotriazolopyrimidines and evaluation of their anti-soybean lipoxygenase, anti-xanthine oxidase, and cytotoxic activities
  作者：Abderrahim Ben Saïd、Anis Romdhane、Nicolas Elie、David Touboul、Hichem Ben Jannet、Jalloul Bouajila

  DOI：10.3109/14756366.2015.1118684

  日期：2016.11.1

  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).