3-bromo-4-(4-fluorobenzyloxy)benzaldehyde | 428484-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-4-(4-fluorobenzyloxy)benzaldehyde
• 英文别名: 3-Bromo-4-[(4-fluorophenyl)methoxy]benzaldehyde
• CAS: 428484-82-6
• 化学式: C₁₄H₁₀BrFO₂
• mdl: MFCD02605292
• 分子量: 309.135
• InChiKey: YSVWEXDJFVACDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮 、 3-bromo-4-(4-fluorobenzyloxy)benzaldehyde 在 哌啶 作用下， 以 乙醇 为溶剂， 以98%的产率得到(Z)-5-[3-bromo-4-(4-fluorobenzyloxy)benzylidene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects

  摘要：

  Benzylidene-2,4-thiazolidinedione derivatives with substitutions on the phenyl ring at the ortho or para positions of the thiazolidinedione (TZD) group were synthesized as PTP1B inhibitors with IC50 values in a low micromolar range. Compound 3e, the lowest, bore an IC50 of 5.0 mu M. In vivo efficacy of 3e as an antiobesity and hypoglycemic agent was evaluated in a mouse model system. Significant improvement of glucose tolerance was observed. This compound also significantly suppressed weight gain and significantly improved blood parameters such as TG, total cholesterol and NEFA. Compound 3e was also found to activate peroxisome proliferator-activated receptors (PPARs) indicating multiple mechanisms of action. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.020
• 作为产物：
  描述：

  3-溴-4-羟基苯甲醛 、 4-氟氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以97%的产率得到3-bromo-4-(4-fluorobenzyloxy)benzaldehyde
  参考文献：
  名称：

  Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects

  摘要：

  Benzylidene-2,4-thiazolidinedione derivatives with substitutions on the phenyl ring at the ortho or para positions of the thiazolidinedione (TZD) group were synthesized as PTP1B inhibitors with IC50 values in a low micromolar range. Compound 3e, the lowest, bore an IC50 of 5.0 mu M. In vivo efficacy of 3e as an antiobesity and hypoglycemic agent was evaluated in a mouse model system. Significant improvement of glucose tolerance was observed. This compound also significantly suppressed weight gain and significantly improved blood parameters such as TG, total cholesterol and NEFA. Compound 3e was also found to activate peroxisome proliferator-activated receptors (PPARs) indicating multiple mechanisms of action. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.020