1-(2-丁氧基乙氧基)-4-碘-2,5-二甲基苯 | 920270-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(2-丁氧基乙氧基)-4-碘-2,5-二甲基苯
• 英文名称: 1-(2-butoxyethoxy)-4-iodo-2,5-dimethylbenzene
• CAS: 920270-43-5
• 化学式: C₁₄H₂₁IO₂
• 分子量: 348.224
• InChiKey: AJOLEZQXRXQKFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-丁氧基乙氧基)-4-碘-2,5-二甲基苯 、 4-碘苯甲酸甲酯 在 叔丁基锂 、 zinc dibromide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 、 正己烷 、 N-甲基吡咯烷酮 为溶剂， 反应 17.0h， 生成 Methyl 4-[4-(2-butoxyethoxy)-2,5-dimethylphenyl]benzoate
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Analysis of Isoform-Selective Retinoic Acid Receptor β Ligands

  摘要：

  We recently discovered the isoform selective RAR beta 2 ligand 4'-octyl-4-biphenylcarboxylic acid (3, AC-55649). Although 3 is highly potent at RAR beta 2 and displays excellent selectivity, solubility issues make it unsuitable for drug development. Herein we describe the exploration of the SAR in a biphenyl and a phenylthiazole series of analogues of 3. This ultimately led to the design of 28, a novel, orally available ligand with excellent isoform selectivity for the RAR beta 2.

  DOI：

  10.1021/jm801532e
• 作为产物：
  描述：

  2-丁氧基乙基溴 、 4-碘-2,5-二甲基苯酚 在 氢氧化钾 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以34%的产率得到1-(2-丁氧基乙氧基)-4-碘-2,5-二甲基苯
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Analysis of Isoform-Selective Retinoic Acid Receptor β Ligands

  摘要：

  We recently discovered the isoform selective RAR beta 2 ligand 4'-octyl-4-biphenylcarboxylic acid (3, AC-55649). Although 3 is highly potent at RAR beta 2 and displays excellent selectivity, solubility issues make it unsuitable for drug development. Herein we describe the exploration of the SAR in a biphenyl and a phenylthiazole series of analogues of 3. This ultimately led to the design of 28, a novel, orally available ligand with excellent isoform selectivity for the RAR beta 2.

  DOI：

  10.1021/jm801532e

文献信息

• COMPOUNDS WITH ACTIVITY AT RETINOIC ACID RECEPTORS
  申请人：Olsson Roger

  公开号：US20090176837A1

  公开（公告）日：2009-07-09

  Disclosed herein are novel compounds with activity at RARβ 2 receptors. Further disclosed are the use of such compounds for treatment of or to alleviate symptoms of cancer, neurological disorders such as memory deficits and schizophrenia, neurodegenerative disorders such as Parkinson's and Alzheimer's diseases, inflammatory disorders such as psoriasis and rheumatoid arthritis, eye disorders and depression.

  本文揭示了具有对RARβ 2受体活性的新化合物。进一步揭示了这些化合物的用途，用于治疗或缓解癌症、神经系统疾病（如记忆障碍和精神分裂症）、神经退行性疾病（如帕金森病和阿尔茨海默病）、炎症性疾病（如银屑病和类风湿性关节炎）、眼部疾病和抑郁症状。
• [EN] COMPOUNDS WITH ACTIVITY AT RETINOIC ACID RECEPTORS<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE AU NIVEAU DES RECEPTEURS DE L'ACIDE RETINOIQUE
  申请人：ACADIA PHARM INC

  公开号：WO2007009083A2

  公开（公告）日：2007-01-18

  [EN] Disclosed herein are novel compounds with activity at RARß 2 receptors. Further disclosed are the use of such compounds for treatment of or to alleviate symptoms of cancer, neurological disorders such as memory deficits and schizophrenia, neurodegenerative disorders such as Parkinson's and Alzheimer's diseases, inflammatory disorders such as psoriasis and rheumatoid arthritis, eye disorders and depression.
  [FR] L'invention se rapporte à de nouveaux composés présentant une activité au niveau des récepteurs de RARß 2. Cette invention concerne en outre l'utilisation de ces composés pour traiter le cancer, des troubles neurologiques tels que des déficiences de la mémoire et la schizophrénie, des troubles nerodégénératifs tels que la maladie de Parkinson et la maladie d'Alzheimer, des troubles inflammatoires tels que le psoriasis et l'arthrite rhumatoïde, des troubles oculaires, et la dépression, ou pour atténuer les symptômes de ces différentes affections.
• Design, Synthesis, and Structure−Activity Analysis of Isoform-Selective Retinoic Acid Receptor β Ligands
  作者：Birgitte W. Lund、Anne Eeg Knapp、Fabrice Piu、Natalie K. Gauthier、Mikael Begtrup、Uli Hacksell、Roger Olsson

  DOI：10.1021/jm801532e

  日期：2009.3.26

  We recently discovered the isoform selective RAR beta 2 ligand 4'-octyl-4-biphenylcarboxylic acid (3, AC-55649). Although 3 is highly potent at RAR beta 2 and displays excellent selectivity, solubility issues make it unsuitable for drug development. Herein we describe the exploration of the SAR in a biphenyl and a phenylthiazole series of analogues of 3. This ultimately led to the design of 28, a novel, orally available ligand with excellent isoform selectivity for the RAR beta 2.