2-(5-(4-nitrophenyl)-6-bromo-6H-1,3,4-oxadiazin-2-yl)acetonitrile | 1300095-98-0

• 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: 2-(5-(4-nitrophenyl)-6-bromo-6H-1,3,4-oxadiazin-2-yl)acetonitrile
• 英文别名: 2-[6-bromo-5-(4-nitrophenyl)-6H-1,3,4-oxadiazin-2-yl]acetonitrile
• CAS: 1300095-98-0
• 化学式: C₁₁H₇BrN₄O₃
• 分子量: 323.106
• InChiKey: SSAWIZHFASCHIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-(4-nitrophenyl)-6-bromo-6H-1,3,4-oxadiazin-2-yl)acetonitrile 在 四(三苯基膦)钯 、 sodium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 21.0h， 生成 2-(4-nitroacetophenon-α-yl)-3-(4-nitrophenyl)-5-cyano-6-(cyanomethyl)pyran
  参考文献：
  名称：

  Anti-tumor and anti-leishmanial evaluations of 1,3,4-oxadiazine, pyran derivatives derived from cross-coupling reactions of β-bromo-6H-1,3,4-oxadiazine derivatives

  摘要：

  Cyanoacetylhydrazine reacted with the omega-bromoacetophenones 2a,b to give hydrazide-hydrazone derivatives 3a,b. The latter products were cyclized to the 1,3,4-oxadiazine derivatives 4a,b. Bromination of the latter products gave the 6-bromo-6H-1,3,4-oxadiazine derivatives 5a,b which underwent a series of cross-coupling reactions. The antitumor evaluation of the newly synthesized products against the three cancer cells namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of them have high inhibitory effect towards three cell lines which is higher than the standard. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.051
• 作为产物：
  描述：

  2-(5-(4-nitrophenyl)-6H-1,3,4-oxadiazin-2-yl)acetonitrile 在 溴 、 溶剂黄146 作用下， 反应 0.5h， 以83%的产率得到2-(5-(4-nitrophenyl)-6-bromo-6H-1,3,4-oxadiazin-2-yl)acetonitrile
  参考文献：
  名称：

  Anti-tumor and anti-leishmanial evaluations of 1,3,4-oxadiazine, pyran derivatives derived from cross-coupling reactions of β-bromo-6H-1,3,4-oxadiazine derivatives

  摘要：

  Cyanoacetylhydrazine reacted with the omega-bromoacetophenones 2a,b to give hydrazide-hydrazone derivatives 3a,b. The latter products were cyclized to the 1,3,4-oxadiazine derivatives 4a,b. Bromination of the latter products gave the 6-bromo-6H-1,3,4-oxadiazine derivatives 5a,b which underwent a series of cross-coupling reactions. The antitumor evaluation of the newly synthesized products against the three cancer cells namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of them have high inhibitory effect towards three cell lines which is higher than the standard. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.051