2-bromo-5-(4-methoxy-2-methylphenyl)thiophene | 1430419-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-5-(4-methoxy-2-methylphenyl)thiophene
• 英文别名: 2-Bromo-5-(4-methoxy-2-methylphenyl)thiophene
• CAS: 1430419-07-0
• 化学式: C₁₂H₁₁BrOS
• 分子量: 283.189
• InChiKey: HOJBJLUAWOABSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(4-methoxy-2-methylphenyl)thiophene 、 2-氯-4-甲氧基苯硼酸 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以58%的产率得到2-(2-chloro-4-methoxyphenyl)-5-(4-methoxy-2-methylphenyl)thiophene
  参考文献：
  名称：

  Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

  摘要：

  To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selective. Most of the bis(hydroxyphenyl)-thiophenes were ER beta selective, whereas the tris(hydroxyphenyl)-thiophenese were ER alpha selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity, in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11 Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.

  DOI：

  10.1021/jm400157e

文献信息

• Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity
  作者：Jian Min、Pengcheng Wang、Sathish Srinivasan、Jerome C. Nwachukwu、Pu Guo、Minjian Huang、Kathryn E. Carlson、John A. Katzenellenbogen、Kendall W. Nettles、Hai-Bing Zhou

  DOI：10.1021/jm400157e

  日期：2013.4.25

  To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selective. Most of the bis(hydroxyphenyl)-thiophenes were ER beta selective, whereas the tris(hydroxyphenyl)-thiophenese were ER alpha selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity, in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11 Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.