(E)-2,6-di-tert-butyl-4-(4-methoxystyryl)phenol | 116376-66-0

• 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: (E)-2,6-di-tert-butyl-4-(4-methoxystyryl)phenol
• 英文别名: 2,6-Di-tert-butyl-4-[(E)-2-(4-methoxy-phenyl)-vinyl]-phenol；2,6-Di-tert-butyl-4-[2-(4-methoxy-phenyl)-vinyl]-phenol；2,6-ditert-butyl-4-[(E)-2-(4-methoxyphenyl)ethenyl]phenol
• CAS: 116376-66-0
• 化学式: C₂₃H₃₀O₂
• 分子量: 338.49
• InChiKey: KEMYDSIZEFZYSK-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,6-di-tert-butyl-4-(4-methoxystyryl)phenol 在 吡啶盐酸盐 作用下， 生成 4-{(E)-2-[3,5-Di-tert-butyl-4-(2-hydroxy-3-isopropylamino-propoxy)-phenyl]-vinyl}-phenol
  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：

  对甲氧基苯乙酸 、 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， 反应 7.0h， 生成 (E)-2,6-di-tert-butyl-4-(4-methoxystyryl)phenol
  参考文献：
  名称：

  Effect of structure on potency and selectivity in 2,6-disubstituted-4-(2-arylethenyl)phenol lipoxygenase inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm00169a010

文献信息

• 10.1021/acs.orglett.4c00839
  作者：Nagasawa, Shota、Itagaki, Yudai、Sasano, Yusuke、Iwabuchi, Yoshiharu

  DOI：10.1021/acs.orglett.4c00839

  日期：——

  Aerobic oxidative dimerization of hydroxystilbenoids is described. A Cr–salen complex catalyzed the dimerization of hydroxystilbenoids in 1,1,1,3,3,3-hexafluoroisopropanol to form compounds comprising a natural product-like scaffold (quadrangularin) or its precursor depending on the aromatic substituents. The addition of a catalytic amount of scandium triflate [Sc(OTf)3] to the reaction system altered

  描述了羟基二苯乙烯类化合物的有氧氧化二聚。 Cr-salen 络合物催化 1,1,1,3,3,3-六氟异丙醇中羟基二苯乙烯类化合物的二聚，形成包含天然产物样支架（四边形）或其前体（取决于芳香族取代基）的化合物。向反应体系中添加催化量的三氟甲磺酸钪[Sc(OTf) 3 ]改变了反应结果，得到了不同的天然产物样化合物，苍白球醇型二聚体。
• Antiinflammatory 2,6-di-tert-butyl-4-(2-arylethenyl)phenols
  作者：Edward S. Lazer、Hin Chor Wong、Genus J. Possanza、Anne G. Graham、Peter R. Farina

  DOI：10.1021/jm00121a021

  日期：1989.1

  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.
• ARNOLDI, ANNA;CARUGHI, MARICA;FARINA, GANDOLFINA;MERLINI, LUCIO;PARRINO, +, J. AGR. AND FOOD CHEM., 37,(1989) N, C. 508-512
  作者：ARNOLDI, ANNA、CARUGHI, MARICA、FARINA, GANDOLFINA、MERLINI, LUCIO、PARRINO, +

  DOI：——

  日期：——
• Linked aryl aryloxypropanolamines as a new class of lipid catabolic agents
  作者：Michael T. Cox、Stuart E. Jaggers、Geraint Jones

  DOI：10.1021/jm00200a008

  日期：1978.2

  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.
• 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.