4-[(5,8-Diphenylnaphthalene-2-carbonyl)amino]-3-fluorobenzoic acid | 1582776-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(5,8-Diphenylnaphthalene-2-carbonyl)amino]-3-fluorobenzoic acid
• 英文别名: 4-[(5,8-diphenylnaphthalene-2-carbonyl)amino]-3-fluorobenzoic acid
• CAS: 1582776-50-8
• 化学式: C₃₀H₂₀FNO₃
• 分子量: 461.492
• InChiKey: ORCXYNFMZGFHMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲酸甲酯 在 copper(l) iodide 、 三氟甲磺酸 、 bis-(pyridine)iodonium(I) tetrafluoroborate 、 (1S,2S)-(+)-1,2-环己二胺 、 sodium carbonate 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 4-[(5,8-Diphenylnaphthalene-2-carbonyl)amino]-3-fluorobenzoic acid
  参考文献：
  名称：

  Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold

  摘要：

  Arotinoids containing a C5,C8-diphenylnaphthalene-2-y1 ring linked to a (C3-halogenated) benzoic acid via an ethenyl connector (but not the corresponding naphthamides), which are prepared by Horner-Wadsworth-Emmons reaction of naphthaldehydes and benzylphosphonates, display the rather unusual property of being RXR agonists (15-fold induction of the RXR reporter cell line was achieved at 3- to 10-fold lower concentration than 9-cis-retinoic acid) and RAR antagonists as shown by transient transactivation studies. The binding of such bulky ligands suggests that the RXR ligand-binding domain is endowed with some degree of structural elasticity.

  DOI：

  10.1021/ml400521f

文献信息

• Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold
  作者：Claudio Martínez、Michele Lieb、Susana Álvarez、Fátima Rodríguez-Barrios、Rosana Álvarez、Harshal Khanwalkar、Hinrich Gronemeyer、Angel R. de Lera

  DOI：10.1021/ml400521f

  日期：2014.5.8

  Arotinoids containing a C5,C8-diphenylnaphthalene-2-y1 ring linked to a (C3-halogenated) benzoic acid via an ethenyl connector (but not the corresponding naphthamides), which are prepared by Horner-Wadsworth-Emmons reaction of naphthaldehydes and benzylphosphonates, display the rather unusual property of being RXR agonists (15-fold induction of the RXR reporter cell line was achieved at 3- to 10-fold lower concentration than 9-cis-retinoic acid) and RAR antagonists as shown by transient transactivation studies. The binding of such bulky ligands suggests that the RXR ligand-binding domain is endowed with some degree of structural elasticity.