[3-[3-(1-adamantyl)-4-methoxyphenyl]-2H-1-benzopyran]-7-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: [3-[3-(1-adamantyl)-4-methoxyphenyl]-2H-1-benzopyran]-7-carboxylic acid
• 英文别名: 3-(3-Adamantan-1-yl-4-methoxy-phenyl)-2H-chromene-7-carboxylic acid；3-[3-(1-adamantyl)-4-methoxyphenyl]-2H-chromene-7-carboxylic acid
• 化学式: C₂₇H₂₈O₄
• 分子量: 416.517
• InChiKey: HCERSGNVDIKWSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(1-Adamantyl)-4-methoxyphenylethanone 在 溴 作用下， 以 乙醚 为溶剂， 生成 [3-[3-(1-adamantyl)-4-methoxyphenyl]-2H-1-benzopyran]-7-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activities of new heterocyclic aromatic retinoids

  摘要：

  A series of 3-aryl-2H-1-benzopyrancarboxylic acid derivatives was synthesized and evaluated as Retinoic Acid Receptor (RAR) agonists. By modifications of the 3-aryl group, we have obtained new retinoids exhibiting potent cellular differentiating activities and high affinities for RARs. Moreover, hydrogenation of the 2H-1-benzopyran ring led to the 3-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-naphthalen-2-yl)-3,4-dihydro-2H-1-benzopyran-7-yl carboxylic acid, characterized by a RAR beta binding profile. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00405-8

文献信息

• Utilisation de rétinoides en tant qu'agent induisant la pigmentation
  申请人：CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES GALDERMA (C.I.R.D. GALDERMA)

  公开号：EP0862910B1

  公开（公告）日：2003-05-02
• US5849798A
  申请人：——

  公开号：US5849798A

  公开（公告）日：1998-12-15
• Synthesis and biological activities of new heterocyclic aromatic retinoids
  作者：P. Diaz、S. Michel、L. Stella、B. Charpentier

  DOI：10.1016/s0960-894x(97)00405-8

  日期：1997.9

  A series of 3-aryl-2H-1-benzopyrancarboxylic acid derivatives was synthesized and evaluated as Retinoic Acid Receptor (RAR) agonists. By modifications of the 3-aryl group, we have obtained new retinoids exhibiting potent cellular differentiating activities and high affinities for RARs. Moreover, hydrogenation of the 2H-1-benzopyran ring led to the 3-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-naphthalen-2-yl)-3,4-dihydro-2H-1-benzopyran-7-yl carboxylic acid, characterized by a RAR beta binding profile. (C) 1997 Elsevier Science Ltd.