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Design, Synthesis and Antibacterial Activity of Novel Pyrimidine‐Containing 4 H ‐Chromen‐4‐One Derivatives **
Author(s) -
Su Shijun,
Chen Mei,
Tang Xuemei,
Peng Feng,
Liu Tingting,
Zhou Qing,
Zhan Wenliang,
He Ming,
Xie Chengwei,
Xue Wei
Publication year - 2021
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202100186
Subject(s) - ralstonia solanacearum , xanthomonas oryzae , chemistry , antibacterial activity , sulfanyl , xanthomonas oryzae pv. oryzae , pyrimidine , reagent , nuclear chemistry , stereochemistry , bacteria , pathogen , microbiology and biotechnology , biochemistry , organic chemistry , biology , genetics , gene
A series of pyrimidine‐containing 4 H ‐chromen‐4‐one derivatives were designed and synthesized by combining bioactive substructures. Preliminary biological activity results showed that most of the compounds displayed significant inhibitory activities in vitro against Xanthomonas axonopodis pv. Citri ( X. axonopodis ), Xanthomonas oryzae pv. oryzae ( X. oryzae ) and Ralstonia solanacearum ( R. solanacearum ). In particular, compound 2‐[(3‐{[5,7‐dimethoxy‐4‐oxo‐2‐(3,4,5‐trimethoxyphenyl)‐4 H ‐1‐benzopyran‐3‐yl]oxy}propyl)sulfanyl]‐4‐(4‐methylphenyl)‐6‐oxo‐1,6‐dihydropyrimidine‐5‐carbonitrile ( 4c ) demonstrated a good inhibitory effect against X. axonopodis and X. oryzae , with the half‐maximal effective concentration (EC 50 ) values of 15.5 and 14.9 μg/mL, respectively, and compound 2‐[(3‐{[5,7‐Dimethoxy‐4‐oxo‐2‐(3,4,5‐trimethoxyphenyl)‐4 H ‐1‐benzopyran‐3‐yl]oxy}propyl)sulfanyl]‐4‐(3‐fluorophenyl)‐6‐oxo‐1,6‐dihydropyrimidine‐5‐carbonitrile ( 4h ) showed the best antibacterial activity against R. solanacearum with an EC 50 value of 14.7 μg/mL. These results were better than commercial reagents bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL, respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative (42.4 %) and protective (49.2 %) activities for rice bacterial leaf blight than BT (35.2, 39.1 %) and TC (30.8, 27.3 %). The mechanism of compound 4c against X. oryzae was analyzed through scanning electron microscopy (SEM). These results indicated that pyrimidine‐containing 4 H ‐chromen‐4‐one derivatives have important value in the research of new agrochemicals.