4-[(5-Benzoyl-4-phenyl-1,3-thiazol-2-yl)amino]benzonitrile | 1375644-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(5-Benzoyl-4-phenyl-1,3-thiazol-2-yl)amino]benzonitrile
• CAS: 1375644-31-7
• 化学式: C₂₃H₁₅N₃OS
• 分子量: 381.458
• InChiKey: UUKMLVLBCSKLKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-[Amino(phenyl)methylidene]-3-(4-cyanophenyl)thiourea 、 2-溴苯乙酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到4-[(5-Benzoyl-4-phenyl-1,3-thiazol-2-yl)amino]benzonitrile
  参考文献：
  名称：

  Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE2 production in cells

  摘要：

  This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE(2) reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R-2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R-1 = Me, R-2 = 4-OPh-Ph, R-3 = CH(OH)Me) exhibited the most potent cellular PGE(2) reducing activity of the entire series (EC50 = 90 nM) with an IC50 value for COX-2 inhibition of >5 mu M in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.013