2,6-Di-tert-butyl-4-[2-(4-fluoro-phenyl)-vinyl]-phenol | 116376-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,6-Di-tert-butyl-4-[2-(4-fluoro-phenyl)-vinyl]-phenol
• 英文别名: 2,6-ditert-butyl-4-[(E)-2-(4-fluorophenyl)ethenyl]phenol
• CAS: 116376-70-6
• 化学式: C₂₂H₂₇FO
• 分子量: 326.454
• InChiKey: AUOKEZXZYUROIC-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-Di-tert-butyl-4-[2-(4-fluoro-phenyl)-vinyl]-phenol 、 异丙胺 、 环氧氯丙烷 生成 1-{2,6-Di-tert-butyl-4-[(E)-2-(4-fluoro-phenyl)-vinyl]-phenoxy}-3-isopropylamino-propan-2-ol
  参考文献：
  名称：

  Linked aryl aryloxypropanolamines as a new class of lipid catabolic agents

  摘要：

  The synthesis of a series of stilbene, biaryl, tolane, diaryl ether, sulfide, sulfoxide, and sulfone oxypropanolamines as potential antiobesity agents is described. These compounds were evaluated in a mouse lipid catabolism screen, and the more active members of the series, 4, 57, and 58, were further investigated in rats and dogs. 1-(2,6-Ditert-butyl-4-trans-styrylphenoxy)-3-isopropylamino-2-propanol (4) possessed considerable lipid catabolic activity in mice and caused a significant reduction in the body weight of rats after 5 weeks and of dogs after 6 weeks. Only hematological irregularities in a chronic toxicity study precluded further development of this compound as an alternative antiobesity treatment.

  DOI：

  10.1021/jm00200a008
• 作为产物：
  描述：

  4-氟苯乙酸 、 3,5-二叔丁基-4-羟基苯甲醛 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 生成 2,6-Di-tert-butyl-4-[2-(4-fluoro-phenyl)-vinyl]-phenol
  参考文献：
  名称：

  Antiinflammatory 2,6-di-tert-butyl-4-(2-arylethenyl)phenols

  摘要：

  A series of 2,6-di-tert-butyl-4-(2-arylethenyl)phenols was prepared and examined for their ability to inhibit cyclooxygenase and 5-lipoxygenase in vitro and developing adjuvant arthritis in vivo in the rat. Structure-activity relationships are discussed. Among the best compounds is (E)-2,6-di-tert-butyl-4-[2-(3-pyridinyl)ethenyl]phenol (7d). It has an IC50 of 0.67 microM for cyclooxygenase and 2.7 microM for 5-lipoxygenase and an ED50 of 2.1 mg/kg in developing adjuvant arthritis. Additional in vivo data are reported for 7d.

  DOI：

  10.1021/jm00121a021

文献信息

• Effect of structure on potency and selectivity in 2,6-disubstituted-4-(2-arylethenyl)phenol lipoxygenase inhibitors
  作者：Edward S. Lazer、Hin Chor Wong、Craig D. Wegner、Anne G. Graham、Peter R. Farina

  DOI：10.1021/jm00169a010

  日期：1990.7

  A series of 2,6-disubstituted 4-(2-arylethenyl)phenols with potent human neutrophil 5-lipoxygenase (5-LO) inhibiting activity (IC50S in the 10(-7) M range) and weaker human platelet cyclooxygenase (CO) inhibiting activity (IC50S in the 10(-6) M range) is described. This series evolved from the chemical modification of an antiinflammatory dual CO/5-LO inhibitor, 2,6-di-tert-butyl-4-[2-(3-pyridyl)ethenyl]phenol (BI-L-93 BS). The potency and selectivity for 5-LO inhibition is greatly influenced by the nature of the substituents in the 2- and 6-positions. Other structure-activity relationships that determine relative 5-LO and CO potency are discussed. In vivo activity against antigen-induced leukotriene-mediated bronchoconstriction and cell influx in guinea pigs is presented. Representatives of the series are active when administered at 30 mg/kg ip.