Synthesis and biological activities of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety

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• 作者：Bo-Ren Yan ; Xin-Yang Lv ; Huan Du ; Man-Ni Gao ; Jian Huang ; Xiao-Ping Bao
• 关键词：quinazolinone ; 1 ; 2 ; 4 ; triazolylthioether ; antimicrobial activity ; synthesis
• 刊名：Chemical Papers
• 出版年：2016
• 出版时间：July 2016
• 年：2016
• 卷：70
• 期：7
• 页码：983-993
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry/Food Science, general; Industrial Chemistry/Chemical Engineering; Biochemistry, general; Medicinal Chemistry; Materials Science, general; Biotechnology;
• 出版者：Springer International Publishing
• ISSN：1336-9075
• 卷排序：70

文摘

A series of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety were synthesised and their antimicrobial activities were evaluated. All the target compounds were characterised by 1H NMR, 13C NMR, ESI-MS, IR and elemental analyses. The single crystal structure of 3-((5-((2-fluorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIi) was also determined. The preliminary bioassays indicated that some of the target compounds possessed good antimicrobial activities. For example, 3-((4-phenyl-5-((4-(trifluoromethyl)benzyl)thio)-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIs) exhibited the best inhibitory effect against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri with the half-effective concentration (EC₅₀) values of 47.6 μg mL−1 and 22.1 μg mL−1, respectively, which were superior to the commercial bactericide, bismerthiazol. Meanwhile, 3-((5-((4-chlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIh) exhibited better fungicidal activities against Pellicularia sasakii and Colletotrichum capsici at the concentration of 50 μg mL−1, in comparison with the commercial fungicide, hymexazol.