4-(3-methoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one | 1261145-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-methoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one
• 英文别名: 4-(3-methoxy-4-prop-2-ynoxyphenyl)but-3-en-2-one
• CAS: 1261145-34-9
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: IYPDVGZTNAGQLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(3-methoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one 、 2,3,4-三甲氧基苯甲醛 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以47%的产率得到1-(3-methoxy-4-prop-2-ynyloxy-phenyl)-5-(2,3,4-trimethoxy-phenyl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds

  摘要：

  A targeted series of chalcone and dienone hybrid compounds containing aminoquinoline and nucleoside templates was synthesized and evaluated for in vitro antimalarial activity. The Cu(I)-catalyzed cycloaddition of azides and terminal alkynes was applied as the hybridization strategy. Several chalcone-chloroquinoline hybrid compounds were found to be notably active, with compound 8b the most active, exhibiting submicromolar IC50 values against the D10, Dd2 and W2 strains of Plasmodium falciparum. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.009
• 作为产物：
  描述：

  香草醛縮丙酮 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 4-(3-methoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  Design, synthesis, and biological and docking studies of novel epipodophyllotoxin–chalcone hybrids as potential anticancer agents

  摘要：

  基于点击化学的设计和高效合成卫春素-香豆素共轭物，作为潜在的拓扑异构酶II抑制剂，以开发更好的抗癌药物前导。

  DOI：

  10.1039/c4md00325j

文献信息

• Design, synthesis, and biological and docking studies of novel epipodophyllotoxin–chalcone hybrids as potential anticancer agents
  作者：Abid Hussain Banday、Vinod V. Kulkarni、Victor J. Hruby

  DOI：10.1039/c4md00325j

  日期：——

  Click-chemistry based design and efficient synthesis of podophyllotoxin–chalcone conjugates as potential topoisomerase-II inhibitors towards the development of better anticancer leads.

  基于点击化学的设计和高效合成卫春素-香豆素共轭物，作为潜在的拓扑异构酶II抑制剂，以开发更好的抗癌药物前导。
• Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds
  作者：Eric M. Guantai、Kanyile Ncokazi、Timothy J. Egan、Jiri Gut、Philip J. Rosenthal、Peter J. Smith、Kelly Chibale

  DOI：10.1016/j.bmc.2010.10.009

  日期：2010.12

  A targeted series of chalcone and dienone hybrid compounds containing aminoquinoline and nucleoside templates was synthesized and evaluated for in vitro antimalarial activity. The Cu(I)-catalyzed cycloaddition of azides and terminal alkynes was applied as the hybridization strategy. Several chalcone-chloroquinoline hybrid compounds were found to be notably active, with compound 8b the most active, exhibiting submicromolar IC50 values against the D10, Dd2 and W2 strains of Plasmodium falciparum. (C) 2010 Elsevier Ltd. All rights reserved.