(E)-2-(3,4-dimethoxystyryl)-2H-pyran-4(3H)-one | 1380293-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(3,4-dimethoxystyryl)-2H-pyran-4(3H)-one
• 英文别名: 2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-2,3-dihydropyran-4-one
• CAS: 1380293-80-0
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: PGCSDHCWFKTIKR-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,4-dimethoxystyryl)-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85%的产率得到(E)-2-(3,4-dimethoxystyryl)-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：

  3,4-二甲氧基苯乙烯 、 2-乙烯基-2,3-二氢吡喃-4-酮 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 copper(l) iodide 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(E)-2-(3,4-dimethoxystyryl)-2H-pyran-4(3H)-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

文献信息

• 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.