5-(4-octyl-phenyl)-thiophene-2-carboxylic acid | 1130165-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(4-octyl-phenyl)-thiophene-2-carboxylic acid
• 英文别名: 5-(4-Octylphenyl)thiophene-2-carboxylic acid
• CAS: 1130165-68-2
• 化学式: C₁₉H₂₄O₂S
• 分子量: 316.464
• InChiKey: QVBBOYJFBDQZLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 5-(4-octylphenyl)-2-thiophenecarboxylate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以98%的产率得到5-(4-octyl-phenyl)-thiophene-2-carboxylic acid
  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

• 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.