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Design, synthesis, antiviral bioactivity and three‐dimensional quantitative structure–activity relationship study of novel ferulic acid ester derivatives containing quinazoline moiety
Author(s) -
Wu Zengxue,
Zhang Jian,
Chen Jixiang,
Pan Jianke,
Zhao Lei,
Liu Dengyue,
Zhang Awei,
Chen Jin,
Hu Deyu,
Song Baoan
Publication year - 2017
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4579
Subject(s) - ferulic acid , tobacco mosaic virus , quinazoline , moiety , ec50 , chemistry , lead compound , stereochemistry , structure–activity relationship , in vivo , antiviral drug , quantitative structure–activity relationship , biochemistry , virus , pharmacology , biology , in vitro , drug , virology , microbiology and biotechnology
BACKGROUND Ferulic acid and quinazoline derivatives possess good antiviral activities. In order to develop novel compounds with high antiviral activities, a series of ferulic acid ester derivatives containing quinazoline were synthesized and evaluated for their antiviral activities. RESULTS Bioassays indicated that some of the compounds exhibited good antiviral activities in vivo against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). One of the compounds demonstrated significant curative and protective activities against TMV and CMV, with EC 50 values of 162.14, 114.61 and 255.49, 138.81 mg L −1 , respectively, better than those of ningnanmycin (324.51, 168.84 and 373.88, 272.70 mg L −1 ). The values of q 2 and r 2 for comparative molecular field analysis and comparative molecular similarity index analysis in the TMV (0.508, 0.663 and 0.992, 0.930) and CMV (0.530, 0.626 and 0.997, 0.981) models presented good predictive abilities. CONCLUSION Some of the title compounds demonstrated good antiviral activities. Three‐dimensional quantitative structure–activity relationship models revealed that the antiviral activities depend on steric and electrostatic properties. These results could provide significant structural insights for the design of highly active ferulic acid derivatives. © 2017 Society of Chemical Industry