cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid oxime methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid oxime methyl ester
• 英文别名: methyl 4-[(Z)-N-hydroxy-C-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)carbonimidoyl]benzoate
• 化学式: C₂₄H₂₉NO₃
• 分子量: 379.499
• InChiKey: RBGSLFTYXUWTLW-DAFNUICNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid oxime methyl ester 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 39.5h， 生成 cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid O-methylcyclopropyloxime
  参考文献：
  名称：

  Synthesis of Retinoid X Receptor-Specific Ligands That Are Potent Inducers of Adipogenesis in 3T3-L1 Cells

  摘要：

  A novel series of oxime ligands has been synthesized that displays potent, specific activation of the retinoid X receptors (RXRs). The oximes of S-substituted (tetramethyltetrahydronaphthyl)carbonylbenzoic acids are readily available by condensation with hydroxyl- or methoxylamine; alkylation of the hydroxyl oxime provides a variety of analogues. Grimes and variously substituted oxime derivatives demonstrate high binding affinity for the RXRs and specific RXR activation and, hence, are called rexinoids. These oxime rexinoids are activators of the RXR: PPAR gamma heterodimer and are potent inducers of differentiation of 3T3-L1 preadipocytes to adipocytes. We have recently reported that ligands which activate the RXR:PPAR gamma heterodimer in this manner are effective in the treatment of type II diabetes (non-insulin-dependent diabetes mellitus, NIDDM). Thus, these new oxime rexinoids are potential therapeutic agents for the treatment of metabolic disorders, such as obesity and diabetes.

  DOI：

  10.1021/jm980621r

文献信息

• The synthesis of tethered ligand dimers for PPARγ–RXR protein heterodimers
  作者：Debra L. Mohler、Gang Shen

  DOI：10.1039/b600848h

  日期：——

  Heterodimeric compounds based on tethering the PPARγ agonist Rosiglitazone to the RXR ligand Targretin have been prepared.

  基于将PPARγ激动剂罗格列酮与RXR配体他格列汀连接形成的异源二聚体化合物已经制备成功。
• Synthesis of Retinoid X Receptor-Specific Ligands That Are Potent Inducers of Adipogenesis in 3T3-L1 Cells
  作者：Stacie S. Canan Koch、Laura J. Dardashti、Rosemary M. Cesario、Glenn E. Croston、Marcus F. Boehm、Richard A. Heyman、Alex M. Nadzan

  DOI：10.1021/jm980621r

  日期：1999.2.1

  A novel series of oxime ligands has been synthesized that displays potent, specific activation of the retinoid X receptors (RXRs). The oximes of S-substituted (tetramethyltetrahydronaphthyl)carbonylbenzoic acids are readily available by condensation with hydroxyl- or methoxylamine; alkylation of the hydroxyl oxime provides a variety of analogues. Grimes and variously substituted oxime derivatives demonstrate high binding affinity for the RXRs and specific RXR activation and, hence, are called rexinoids. These oxime rexinoids are activators of the RXR: PPAR gamma heterodimer and are potent inducers of differentiation of 3T3-L1 preadipocytes to adipocytes. We have recently reported that ligands which activate the RXR:PPAR gamma heterodimer in this manner are effective in the treatment of type II diabetes (non-insulin-dependent diabetes mellitus, NIDDM). Thus, these new oxime rexinoids are potential therapeutic agents for the treatment of metabolic disorders, such as obesity and diabetes.