methyl 4-<(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoate | 158499-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-<(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoate
• 英文别名: methyl 4-(3'-hydroxy-5',6',7',8'-tetrahydro-5',5',8',8'-tetramethyl-2'-naphthalenylcarbonyl)benzoate；4-[(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester；methyl 4-(3-hydroxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)benzoate
• CAS: 158499-20-8
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: MSBQKTPGPXCJIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-<(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoate 在 氢氧化钾 、 sodium amide 作用下， 以 甲醇 为溶剂， 反应 15.5h， 生成 4-[1-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid
  参考文献：
  名称：

  Boehm; Zhang; Badea, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲基-2,5-己二醇 在 盐酸 、 三氯化铝 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 4-<(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoate
  参考文献：
  名称：

  Boehm; Zhang; Badea, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941

  摘要：

  DOI：

文献信息

• [EN] DIMER-SELECTIVE RXR MODULATORS AND METHODS FOR THEIR USE<br/>[FR] MODULATEURS RXR SELECTIFS POUR LES DIMERES ET LEURS METHODES D'UTILISATION
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：WO1997012853A1

  公开（公告）日：1997-04-10

  (EN) Dimer-selective RXR modulator compounds having agonist, partial agonist and/or antagonist activity in the context of an RXR homodimer and/or RXR heterodimers are provided. Also provided are pharmaceutical compositions incorporating such dimer-selective RXR modulator compounds and methods for their therapeutic use.(FR) Composés modulateurs RXR (des récepteurs X de rétinoïde) ayant un effet agoniste, partiellement agoniste et/ou antagoniste dans le contexte d'un homodimère RXR et/ou d'hétérodimères RXR. L'invention porte également sur des compositions pharmaceutiques incorporant de tels composés modulateurs RXR sélectifs pour les dimères et sur des méthodes d'utilisation thérapeutiques de ces compositions.

  提供了具有RXR同源二聚体和/或RXR异源二聚体中的激动剂、部分激动剂和/或拮抗剂活性的二聚体选择性RXR调节剂化合物。还提供了包含这种二聚体选择性RXR调节剂化合物的药物组合物以及它们的治疗用途的方法。
• Dimer-selective RXR modulators and methods for their use
  申请人：——

  公开号：US20040019072A1

  公开（公告）日：2004-01-29

  Dimer-selective RXR modulator compounds having agonist, partial agonist and/or antagonist activity in the context of an RXR homodimer and/or RXR heterodimers are provided. Also provided are pharmaceutical compositions incorporating such dimer-selective RXR modulator compounds and methods for their therapeutic use.

  提供了在RXR同二聚体和/或RXR异二聚体背景下具有激动剂、部分激动剂和/或拮抗剂活性的选择性二聚体选择性RXR调节剂化合物。还提供了包含这些选择性二聚体选择性RXR调节剂化合物的药物组合物和其治疗用途的方法。
• Determinants of Retinoid X Receptor Transcriptional Antagonism
  作者：Claudio N. Cavasotto、Gang Liu、Sharon Y. James、Peter D. Hobbs、Valerie J. Peterson、Ananyo A. Bhattacharya、Siva K. Kolluri、Xiao-kun Zhang、Mark Leid、Ruben Abagyan、Robert C. Liddington、Marcia I. Dawson

  DOI：10.1021/jm030651g

  日期：2004.8.1

  The synthesis and bloactivity of the retinoid X receptor (RXR) antagonist 4-[(3'-n-butyl-5',6', 7',8'-tetrahydro-5',5',8',8'-tetramethyl-2'-naphthalenyl)(cyclopropylidene)methyl]benzoic acid and several heteroatom-substituted analogues are described. Ligand design was based on the scaffold of the X-methyl RXR-selective agonist analogue and reports that 3'-n-propyl and longer n-alkyl groups conferred RXR antagonism. The transcriptional antagonism of the 3'-n-butyl analogue was demonstrated by its blockade of retinoic acid receptor (RAR) beta expression induced by the RXRalpha/peroxisome proliferator-activated receptor (PPAR) gamma heterodimer complexed with an RXRalpha agonist plus the PPARgamma agonist ciglitazone and the inhibition of 9-cis-RA-induced coactivator SRC-1a recruitment to RXRalpha. Receptor-ligand docking studies using full-atom flexible ligand and flexible receptor suggested that binding of the antagonist to the RXRa antagonist conformation was favored because the salt bridge that formed between the retinoid carboxylate and the RXRalpha helix H5 arginine-321 was far stronger than that formed on its binding to the agonist conformation. The antagonist also blocked activation of RAR subtypes alpha and beta by 9-cis-RA but not that of RARgamma.
• DIMER-SELECTIVE RXR MODULATORS AND METHODS FOR THEIR USE
  申请人：LIGAND PHARMACEUTICALS, INC.

  公开号：EP0873295A1

  公开（公告）日：1998-10-28
• US6545049B1
  申请人：——

  公开号：US6545049B1

  公开（公告）日：2003-04-08