7-(p-hydroxy)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one | 1146978-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(p-hydroxy)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one
• 英文别名: 7-(4-hydroxyphenyl)-9,10,11,12-tetrahydro-7H-naphtho[1,2-b]quinolin-8-one
• CAS: 1146978-79-1
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: ZBJCSIBVDRMBRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对溴甲基苯甲酸 、 7-(p-hydroxy)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.25h， 以27.2%的产率得到4-((4-(8-oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridin-7-yl)phenoxy)methyl)benzoic acid
  参考文献：
  名称：

  Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening

  摘要：

  The general control nonrepressed protein 5 (GCN5) plays a crucial role in many biological processes. Dysregulation of GCN5 has been closely related to various human diseases, especially cancers. Hence, the exploitation of small molecules targeting GCN5 is essential for drug design and academic research. Based on the amplified luminescent proximity homogeneous assay screen methodology, we performed high throughput screening and discovered a novel GCN5 inhibitor DC_G16 with 1,8-acridinedione scaffold. Structure optimization led to the identification of a highly potent inhibitor, namely DC_G16-11 with the half-maximal inhibitory concentration (IC50) value of 6.8 mu M. The binding between DC_G16-11 and GCN5 was demonstrated by NMR and SPR with a K-D of 4.2 mu M. It could also inhibit proliferation and induce cell cycle arrest and apoptosis in cancer cells while it presented minimal effects on normal cells. Herein, DC_G16-11 could be applied as a validated chemical probe for GCN5-related biological function research and presented great potential for clinical disease treatment. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.005
• 作为产物：
  描述：

  1,3-环己二酮 、 1-萘胺 、 对羟基苯甲醛 反应 0.07h， 以94.1%的产率得到7-(p-hydroxy)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one
  参考文献：
  名称：

  Microwave-induced synthesis and anti-microbial activities of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives

  摘要：

  Some new substituted tetrahydroacridin-8-ones and diverse derivatives were synthesized by uncatalysed multi-component reaction of dimedone or cyclohexan-1,3-dione, alpha-naphthylamine and various (o,p,m)-substituted benzaldehydes. The in vitro anti-microbial activities of the prepared compounds were evaluated against some bacteria and fungi strains. The results suggested that the products 2a-g and 4a-g exhibited good inhibitory effect against most of the tested organisms. Especially, 2f, 2g, 4f and 4g were shown to be most effective against Rhodotorula rubra and Aspergillus parasiticus and compounds 2a, 2c, 2g, 4f and 4g proved to be effective with MIC values in the range of 3.9-7.8 mu g/ml. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.07.004