4-[4-(2-Butoxy-ethoxy)-5-methyl-thiazol-2-yl]-2-fluoro-benzoic acid ethyl ester | 905567-14-8

• 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: 4-[4-(2-Butoxy-ethoxy)-5-methyl-thiazol-2-yl]-2-fluoro-benzoic acid ethyl ester
• CAS: 905567-14-8
• 化学式: C₁₉H₂₄FNO₄S
• 分子量: 381.468
• InChiKey: LXBRPNUIJOEQHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.65
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[4-(2-Butoxy-ethoxy)-5-methyl-thiazol-2-yl]-2-fluoro-benzoic acid ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以1.45 g的产率得到4-[4-(2-丁氧基乙氧基)-5-甲基-1,3-噻唑-2-基]-2-氟苯甲酸
  参考文献：
  名称：

  Discovery of a Potent, Orally Available, and Isoform-Selective Retinoic Acid β2 Receptor Agonist

  摘要：

  4'-Octyl-4-biphenylcarboxylic acid (1g, AC-55649) was identified as a highly isoform-selective agonist at the human RAR beta 2 receptor in a functional intact cell-based screening assay. The subsequent hit to lead optimization transformed the lipophilic, poorly soluble hit into a more potent and orally available compound (2, AC-261066) with retained beta 2 selectivity and greatly improved physiochemical properties. Being an isoform-selective RAR beta 2 receptor agonist that discriminates between nuclear receptor isoforms having identical ligand binding domains, 2 will be useful as a pharmacological research tool but also a valuable starting point for drug development.

  DOI：

  10.1021/jm050891r
• 作为产物：
  描述：

  乙基4-氰基-2-氟苯甲酸酯 在 吡啶 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 4-[4-(2-Butoxy-ethoxy)-5-methyl-thiazol-2-yl]-2-fluoro-benzoic acid ethyl ester
  参考文献：
  名称：

  Discovery of a Potent, Orally Available, and Isoform-Selective Retinoic Acid β2 Receptor Agonist

  摘要：

  4'-Octyl-4-biphenylcarboxylic acid (1g, AC-55649) was identified as a highly isoform-selective agonist at the human RAR beta 2 receptor in a functional intact cell-based screening assay. The subsequent hit to lead optimization transformed the lipophilic, poorly soluble hit into a more potent and orally available compound (2, AC-261066) with retained beta 2 selectivity and greatly improved physiochemical properties. Being an isoform-selective RAR beta 2 receptor agonist that discriminates between nuclear receptor isoforms having identical ligand binding domains, 2 will be useful as a pharmacological research tool but also a valuable starting point for drug development.

  DOI：

  10.1021/jm050891r