(E)-1-(2,4-dimethoxyphenyl)-3-(4-prop-2-ynoxyphenyl)prop-2-en-1-one | 1217264-14-6

• 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: (E)-1-(2,4-dimethoxyphenyl)-3-(4-prop-2-ynoxyphenyl)prop-2-en-1-one
• CAS: 1217264-14-6
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: HKHCTPXOOKKZPX-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  4-(3-azido-2-hydroxy-propoxy)-3,5-dimethyl-5H-thiophen-2-one 、 (E)-1-(2,4-dimethoxyphenyl)-3-(4-prop-2-ynoxyphenyl)prop-2-en-1-one 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以19%的产率得到4-[3-(4-{4-[3-(2,4-dimethoxy-phenyl)-3-oxo-propenyl]-phenoxymethyl}-[1,2,3]triazol-1-yl)-2-hydroxy-propoxy]-3,5-dimethyl-5H-thiophen-2-one
  参考文献：
  名称：

  Comparison of the antiplasmodial and falcipain-2 inhibitory activity of β-amino alcohol thiolactone-chalcone and isatin-chalcone hybrids

  摘要：

  The synthesis and biological evaluation of two novel series of natural-product-like hybrids based on the chalcone, thiolactone and isatin scaffolds is herein described. Results for a 36-member beta-amino alcohol triazole library showed that the thiolactone-chalcones, with IC(50)s ranging from 0.68 to 6.08 mu M, were more active against W2 strain Plasmodium falciparum than the isatin-chalcones with IC(50)s of 14.9 mu M or less. Also of interest is falcipain-2 inhibitory activity displayed by the latter, whereas the thiolactone-chalcones lacked enzyme inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.017
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (E)-1-(2,4-dimethoxyphenyl)-3-(4-prop-2-ynoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthetic approach towards ‘click’ modified chalcone based organotriethoxysilanes; UV-Vis study

  摘要：

  报道了通过1,2,3-三唑将共轭查尔酮直接连接到n-丙基三乙氧基硅烷的高效方法。该合成涉及Claisen-Schmidt缩合，然后是铜(I)催化的偶氮-炔烃环加成（CuAAC）反应。

  DOI：

  10.1039/c4ra08724k

文献信息

• Synthetic approach towards ‘click’ modified chalcone based organotriethoxysilanes; UV-Vis study
  作者：Gurjaspreet Singh、Jandeep Singh、Satinderpal Singh Mangat、Aanchal Arora

  DOI：10.1039/c4ra08724k

  日期：——

  The efficient linkage of a conjugate chalcone to n-propyltriethoxysilanes via a 1,2,3-triazole is reported. The synthesis involves a Claisen–Schmidt condensation followed by a copper(i) catalyzed azide–alkyne cycloaddition (CuAAC) reaction.

  报道了通过1,2,3-三唑将共轭查尔酮直接连接到n-丙基三乙氧基硅烷的高效方法。该合成涉及Claisen-Schmidt缩合，然后是铜(I)催化的偶氮-炔烃环加成（CuAAC）反应。
• Comparison of the antiplasmodial and falcipain-2 inhibitory activity of β-amino alcohol thiolactone-chalcone and isatin-chalcone hybrids
  作者：Renate H. Hans、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmcl.2010.02.017

  日期：2010.4

  The synthesis and biological evaluation of two novel series of natural-product-like hybrids based on the chalcone, thiolactone and isatin scaffolds is herein described. Results for a 36-member beta-amino alcohol triazole library showed that the thiolactone-chalcones, with IC(50)s ranging from 0.68 to 6.08 mu M, were more active against W2 strain Plasmodium falciparum than the isatin-chalcones with IC(50)s of 14.9 mu M or less. Also of interest is falcipain-2 inhibitory activity displayed by the latter, whereas the thiolactone-chalcones lacked enzyme inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.