2-(8,8-dimethyl-5-(phenylethynyl)-7,8-dihydronaphthalen-2-yl)-2-oxoacetic acid | 1178898-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(8,8-dimethyl-5-(phenylethynyl)-7,8-dihydronaphthalen-2-yl)-2-oxoacetic acid
• CAS: 1178898-52-6
• 化学式: C₂₂H₁₈O₃
• 分子量: 330.383
• InChiKey: JBIVYNXXZMFEMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(8,8-dimethyl-5-(phenylethynyl)-7,8-dihydronaphthalen-2-yl)-2-oxoacetic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 C₂₂H₁₇ClO₂
  参考文献：
  名称：

  Retinoid receptor subtype-selective modulators through synthetic modifications of RARγ agonists

  摘要：

  A series of retinoids designed to interfere with the repositioning of H12 have been synthesized to identify novel RAR gamma antagonists based on the structure of known RAR gamma agonists. The transcriptional activities of the novel ligands were revealed by cell-based reporting assays, using engineered cells containg RAR subtype-selective fusions of the RAR ligand-binding domains with the yeast GAL4 activator DNA-binding domain and the cognate luciferase reporter gene. Whereas none of the ligands exhibited features of a selective RAR gamma antagonist, some of them are endowed with interesting activities. In particular 24a acts as a pan-RAR agonist that induces at high concentration a higher transactivation potential on RAR alpha than TTNPB and synergizes at low concentration with TTNPB-bound RAR alpha but not RAR beta or RAR gamma. Similarly, 24c synergizes with TTNPB-bound RAR gamma and exhibits RAR alpha,beta antagonist activity. Compounds 24b and 25b are strong RAR alpha,beta-selective antagonists without agonist or antagonist activities for RAR gamma. Compounds 24b and 24c display weak RXR antagonist activity. In addition several pan-antagonists and partial agonist/antagonists have been defined. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.035
• 作为产物：
  描述：

  methyl 2-(7,8-dihydro-8,8-dimethyl-5-(2-phenylethynyl)-naphthalen-2-yl)-2-oxoacetate 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到2-(8,8-dimethyl-5-(phenylethynyl)-7,8-dihydronaphthalen-2-yl)-2-oxoacetic acid
  参考文献：
  名称：

  Retinoid receptor subtype-selective modulators through synthetic modifications of RARγ agonists

  摘要：

  A series of retinoids designed to interfere with the repositioning of H12 have been synthesized to identify novel RAR gamma antagonists based on the structure of known RAR gamma agonists. The transcriptional activities of the novel ligands were revealed by cell-based reporting assays, using engineered cells containg RAR subtype-selective fusions of the RAR ligand-binding domains with the yeast GAL4 activator DNA-binding domain and the cognate luciferase reporter gene. Whereas none of the ligands exhibited features of a selective RAR gamma antagonist, some of them are endowed with interesting activities. In particular 24a acts as a pan-RAR agonist that induces at high concentration a higher transactivation potential on RAR alpha than TTNPB and synergizes at low concentration with TTNPB-bound RAR alpha but not RAR beta or RAR gamma. Similarly, 24c synergizes with TTNPB-bound RAR gamma and exhibits RAR alpha,beta antagonist activity. Compounds 24b and 25b are strong RAR alpha,beta-selective antagonists without agonist or antagonist activities for RAR gamma. Compounds 24b and 24c display weak RXR antagonist activity. In addition several pan-antagonists and partial agonist/antagonists have been defined. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.035