(E)-3-bromo-4-[(5,8-(diphenyl)naphthalene-2-yl)ethenyl]benzoic acid | 1582776-69-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-3-bromo-4-[(5,8-(diphenyl)naphthalene-2-yl)ethenyl]benzoic acid
• 英文别名: 3-bromo-4-[(E)-2-(5,8-diphenylnaphthalen-2-yl)ethenyl]benzoic acid
• CAS: 1582776-69-9
• 化学式: C₃₁H₂₁BrO₂
• 分子量: 505.411
• InChiKey: ITMMMWDPLKILDP-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  34
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-萘甲酸甲酯 在 N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 正丁基锂 、 三氟甲磺酸 、 bis-(pyridine)iodonium(I) tetrafluoroborate 、 二异丁基氢化铝 、 sodium carbonate 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 44.5h， 生成 (E)-3-bromo-4-[(5,8-(diphenyl)naphthalene-2-yl)ethenyl]benzoic 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.