1-(3-methoxy-4-prop-2-ynyloxy-phenyl)-3-(2,3,4-trimethoxy-phenyl)-propenone | 1261145-78-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3-methoxy-4-prop-2-ynyloxy-phenyl)-3-(2,3,4-trimethoxy-phenyl)-propenone
• 英文别名: 1-(3-methoxy-4-prop-2-ynoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1261145-78-1
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: NJPCKVOJFGLDSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(3-methoxy-4-prop-2-ynyloxy-phenyl)-3-(2,3,4-trimethoxy-phenyl)-propenone 、 齐多夫定 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以51%的产率得到(2R,4S,5S)-1-[5-hydroxymethyl-4-(4-(2-methoxy-4-[3-(2,3,4-trimethoxy-phenyl)-acryloyl]-phenoxymethyl)-[1,2,3]triazol-1-yl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  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：

  1-(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)ethan-1-one 、 2,3,4-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.25h， 以78%的产率得到1-(3-methoxy-4-prop-2-ynyloxy-phenyl)-3-(2,3,4-trimethoxy-phenyl)-propenone
  参考文献：
  名称：

  炔属查耳酮的合成，抗疟和抗结核活性

  摘要：

  评估了一系列炔属查耳酮的抗疟和抗结核活性。该系列的抗疟数据表明，恶性疟原虫W2菌株的生长抑制可通过在炔基上邻位引入甲氧基来实现。与结核分枝杆菌H 37 Rv的复制培养相比，大多数化合物对非复制的活性更高，这对现有的抗结核病药物而言是不同寻常的模式。

  DOI：

  10.1016/j.bmcl.2009.12.062

文献信息

• Synthesis, antimalarial and antitubercular activity of acetylenic chalcones
  作者：Renate H. Hans、Eric M. Guantai、Carmen Lategan、Peter J. Smith、Baojie Wan、Scott G. Franzblau、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmcl.2009.12.062

  日期：2010.2

  A series of acetylenic chalcones were evaluated for antimalarial and antitubercular activity. The antimalarial data for this series suggests that growth inhibition of the W2 strain of Plasmodium falciparum can be imparted by the introduction of a methoxy group ortho to the acetylenic group. Most compounds were more active against non-replicating than replicating cultures of Mycobacterium tuberculosis

  评估了一系列炔属查耳酮的抗疟和抗结核活性。该系列的抗疟数据表明，恶性疟原虫W2菌株的生长抑制可通过在炔基上邻位引入甲氧基来实现。与结核分枝杆菌H 37 Rv的复制培养相比，大多数化合物对非复制的活性更高，这对现有的抗结核病药物而言是不同寻常的模式。
• 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.