[2-(4-methoxy-anilino)-4-phenyl-thiazol-5-yl]-phenyl-methanone | 4308-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(4-methoxy-anilino)-4-phenyl-thiazol-5-yl]-phenyl-methanone
• 英文别名: [2-(4-Methoxyanilino)-4-phenyl-1,3-thiazol-5-yl]-phenylmethanone
• CAS: 4308-01-4
• 化学式: C₂₃H₁₈N₂O₂S
• 分子量: 386.474
• InChiKey: SZOAMNAWAGGDML-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  609.0±65.0 °C(predicted)
• 密度：
  1.264±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲氧基苯基硫脲 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 0.17h， 生成 [2-(4-methoxy-anilino)-4-phenyl-thiazol-5-yl]-phenyl-methanone
  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

文献信息

• Ziemelis,Z. et al., Doklady Chemistry, 1965, vol. 164, p. 840 - 843
  作者：Ziemelis,Z. et al.

  DOI：——

  日期：——