4-allyl-3-{2-[4-(4-allyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)phenylamino]phenyl}-1H-1,2,4-triazole-5(4H)-thione | 1245567-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-allyl-3-{2-[4-(4-allyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)phenylamino]phenyl}-1H-1,2,4-triazole-5(4H)-thione
• 英文别名: 4-prop-2-enyl-3-[4-[2-(4-prop-2-enyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)anilino]phenyl]-1H-1,2,4-triazole-5-thione
• CAS: 1245567-62-7
• 化学式: C₂₂H₂₁N₇S₂
• 分子量: 447.588
• InChiKey: CCKDLCCWIWWNEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-allyl-2-{2-[4-(2-(allylcarbamothioyl)hydrazinecarbonyl)phenylamino]benzoyl}hydrazinecarbothioamide 在 sodium hydroxide 作用下， 反应 3.0h， 以95%的产率得到4-allyl-3-{2-[4-(4-allyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)phenylamino]phenyl}-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2,4′-bis substituted diphenylamines as anticancer agents and potential epidermal growth factor receptor tyrosine kinase inhibitors

  摘要：

  Four new series of 2,4'-bis diphenylamine hydrazones 14, 2,4'-bis aminothiadiazole 16, 2,4'-bis mercaptotriazole 17-18 and 2,4'-bis mercapto-oxadiazole diphenylamine derivatives 19-20 were synthesized and evaluated for their ability to inhibit EGFR tyrosine kinase. Compound N-ethyl-5-{2-[4(5-(ethylamino)-1,3,4-thiadiazol-2-yl)- phenylaminolphenyl}-1,3,4-thiadiazol-2-amine 16a was the most active enzyme inhibitor (98% inhibition at 10 mu M). Moreover, all compounds that showed enzyme inhibition activity were tested in vitro on human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. The tested compounds exploited potent antitumor activity with IC50 values ranging 0.73-2.38 mu M. Molecular modeling and docking of the synthesized compounds into the active site of EGFR kinase domain showed good agreement with the obtained biological results. The present work represents a novel class of diphenylamine based derivatives with potent cytotoxicity and promising EGFR PTK inhibition activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.072