4.7 Article

Synthesis and antiviral bioactivity of novel (1E, 4E)-1-aryl-5-(2-(quinazolin-4-yloxy)phenyl)-1,4-pentadien-3-one derivatives

Journal

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 63, Issue -, Pages 662-669

Publisher

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2013.02.035

Keywords

(1E, 4E)-1; 4-Pentadien-3-one derivatives; Quinazoline moiety; Tobacco mosaic virus; Cucumber mosaic virus; Antiviral activity

Funding

  1. National Key Program for Basic Research [2010CB 126105]
  2. Key Technologies RD Program [2011BAE06B05-6]
  3. National Natural Science Foundation of China [21132003, 21172048]

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A series of novel (1E, 4E)-1-aryl-5-[2-(quinazolin-4-yloxy)phenyl]-1,4-pentadien-3-one derivatives were designed and synthesized by reacting substituent aldehyde with intermediates 4a-f. Antiviral bioassays indicated that most of the compounds exhibited promising ex vivo antiviral bioactivities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 mu g/mL. The relationship between structure and antiviral activity was also discussed. Compounds 5a, 6e, and 6g could possess appreciable protective bioactivities on TMV ex vivo by approximately 50% (EC50) at 257.7, 320.7 and 243.3 mu g/mL. This study is the first to demonstrate that (1E, 4E)-1-aryl-5-(2-(quinazolin-4-yloxy)phenyl)-1,4-pentadien-3-one can be used to develop potential virucides for plants. (c) 2013 Elsevier Masson SAS. All rights reserved.

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