(E)-2-(4-methoxystyryl)-2H-pyran-4(3H)-one | 1365565-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-(4-methoxystyryl)-2H-pyran-4(3H)-one
• 英文别名: 2-[(E)-2-(4-methoxyphenyl)ethenyl]-2,3-dihydropyran-4-one
• CAS: 1365565-21-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: XLAVUKOAAZDFGY-QPJJXVBHSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  375.2±21.0 °C(predicted)
• 密度：
  1.215±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-methoxystyryl)-2H-pyran-4(3H)-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 以78%的产率得到(E)-2-(4-methoxystyryl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

  摘要：

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.059
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 4-甲氧基肉桂醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以60%的产率得到(E)-2-(4-methoxystyryl)-2H-pyran-4(3H)-one
  参考文献：
  名称：

  Competitive [2,3]- and [1,2]-Oxonium Ylide Rearrangements. Concerted or Stepwise?

  摘要：

  The axial equatorial conformational isomer distribution of the reactant diazoacetoacetate or its metal carbene intermediate is reflected in Rh(II) catalyzed oxonium ylide forming reactions of 3-(trans-2-arylvinyl)tetrahydropyranone-5-diazoacetoacetates that afford diastereoisomeric products for both the symmetry-allowed [2,3)- and the formally symmetry-forbidden [1,2]-oxonium ylide rearrangements.

  DOI：

  10.1021/ol300213u

文献信息

• Competitive [2,3]- and [1,2]-Oxonium Ylide Rearrangements. Concerted or Stepwise?
  作者：Deana M. Jaber、Ryan N. Burgin、Matthew Helper、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1021/ol300213u

  日期：2012.4.6

  The axial equatorial conformational isomer distribution of the reactant diazoacetoacetate or its metal carbene intermediate is reflected in Rh(II) catalyzed oxonium ylide forming reactions of 3-(trans-2-arylvinyl)tetrahydropyranone-5-diazoacetoacetates that afford diastereoisomeric products for both the symmetry-allowed [2,3)- and the formally symmetry-forbidden [1,2]-oxonium ylide rearrangements.
• Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells
  作者：Rosimeire Coura Barcelos、Julio Cezar Pastre、Vanessa Caixeta、Débora Barbosa Vendramini-Costa、João Ernesto de Carvalho、Ronaldo Aloise Pilli

  DOI：10.1016/j.bmc.2012.03.059

  日期：2012.6

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.