3-氟-4-(2,2,2-三氟乙氧基)苯基硼酸 | 947533-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-氟-4-(2,2,2-三氟乙氧基)苯基硼酸
• 中文别名: [3-氟-4-(2,2,2-三氟乙氧基)苯基]硼酸
• 英文名称: (3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl)boronic acid
• 英文别名: 3-fluoro-4-(2,2,2-trifluoroethoxy)benzene-boronic acid；[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]boronic acid
• CAS: 947533-09-7
• 化学式: C₈H₇BF₄O₃
• mdl: MFCD09258747
• 分子量: 237.946
• InChiKey: DPSYYQDRJMHAGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-(((2-bromo-4-methylthiazol-5-yl)methyl)thio)-2-methylphenoxy)acetate 、 3-氟-4-(2,2,2-三氟乙氧基)苯基硼酸 在 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Parallel Chemistry Approach to Identify Novel Nuclear Receptor Ligands Based on the GW0742 Scaffold

  摘要：

  We describe the parallel synthesis of novel analogs of GW0742, a peroxisome proliferator-activated receptor delta (PPAR delta) agonist For that purpose, modified reaction conditions were applied, such as a solid-phase palladium-catalyzed Suzuki coupling. In addition, tetrazole-based compounds were generated as a bioisostere for carboxylic acid-containing ligand GW0742. The new compounds were investigated for their ability to activate PPAR delta mediated transcription and their cross-reactivity with the vitamin D receptor (VDR), another member of the nuclear receptor superfamily. We identified many potent PPAR delta agonists that were less toxic than GW0742, where similar to 65 of the compounds synthesized exhibited partial PPAR delta activity (23-98%) with EC50 values ranging from 0.007-18.2 mu M. Some ligands, such as compound 32, were more potent inhibitors of VDR-mediated transcription with significantly reduced PPAR delta activity than GW0742, however, none of the ligands were completely selective for VDR inhibition over PPAR delta activation of transcription.

  DOI：

  10.1021/acscombsci.7b00066

文献信息

• Parallel Chemistry Approach to Identify Novel Nuclear Receptor Ligands Based on the GW0742 Scaffold
  作者：Kelly A. Teske、Ganesha Rai、Premchendar Nandhikonda、Preetpal S. Sidhu、Belaynesh Feleke、Anton Simeonov、Adam Yasgar、Ajit Jadhav、David J. Maloney、Leggy A. Arnold

  DOI：10.1021/acscombsci.7b00066

  日期：2017.10.9

  We describe the parallel synthesis of novel analogs of GW0742, a peroxisome proliferator-activated receptor delta (PPAR delta) agonist For that purpose, modified reaction conditions were applied, such as a solid-phase palladium-catalyzed Suzuki coupling. In addition, tetrazole-based compounds were generated as a bioisostere for carboxylic acid-containing ligand GW0742. The new compounds were investigated for their ability to activate PPAR delta mediated transcription and their cross-reactivity with the vitamin D receptor (VDR), another member of the nuclear receptor superfamily. We identified many potent PPAR delta agonists that were less toxic than GW0742, where similar to 65 of the compounds synthesized exhibited partial PPAR delta activity (23-98%) with EC50 values ranging from 0.007-18.2 mu M. Some ligands, such as compound 32, were more potent inhibitors of VDR-mediated transcription with significantly reduced PPAR delta activity than GW0742, however, none of the ligands were completely selective for VDR inhibition over PPAR delta activation of transcription.