9-(2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazono)-9H-fluorene-2-carboxylic acid | 1569468-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-(2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazono)-9H-fluorene-2-carboxylic acid
• CAS: 1569468-29-6
• 化学式: C₂₃H₁₄ClN₃O₂S
• 分子量: 431.902
• InChiKey: SCRALYFACBWMSW-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  784.3±70.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.58
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  9-(carbamothioylhydrazinylidene)fluorene-2-carboxylic acid 、 2,4'-二氯苯乙酮 以 乙醇 为溶剂， 以93%的产率得到9-(2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazono)-9H-fluorene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors

  摘要：

  Acetylation, which targets a broad range of histone and non-histone proteins, is a reversible mechanism and plays a critical role in eukaryotic genes activation/deactivation. Acetyltransferases are very well conserved through evolution. This allows the use of a simple model organism, such as budding yeast, for the study of their related processes and to discover specific inhibitors. Following a simple yeast-based chemogenetic approach, we have identified a novel HAT (histone acetyltransferase) inhibitor active both in vitro and in vivo. This new synthetic compound,1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(propan-2-ylidene) hydrazine, named BF1, showed substrate selectivity for histone H3 acetylation and inhibitory activity in vitro on recombinant HAT Gcn5 and p300. Finally, we tested BF1 on human cells, HeLa as control and two aggressive cancer cell lines: a neuroblastoma from neuronal tissue and glioblastoma from brain tumour. Both global acetylation of histone H3 and specific acetylation at lysine 18 (H3AcK18) were lowered by BF1 treatment. Collectively, our results show the efficacy of this novel HAT inhibitor and propose the utilization of BF1 as a new, promising tool for future pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.022