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

Chemical papers, 2016-07, Vol.70 (7), p.983-993 [Peer Reviewed Journal]

Institute of Chemistry, Slovak Academy of Sciences 2016 ;ISSN: 0366-6352 ;EISSN: 1336-9075 ;DOI: 10.1515/chempap-2016-0034

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  • Title:
    Synthesis and biological activities of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety
  • Author: Yan, Bo-Ren ; Lv, Xin-Yang ; Du, Huan ; Gao, Man-Ni ; Huang, Jian ; Bao, Xiao-Ping
  • Subjects: 1,2,4-triazolylthioether ; antimicrobial activity ; Biochemistry ; Biotechnology ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Industrial Chemistry/Chemical Engineering ; Materials Science ; Medicinal Chemistry ; Original Paper ; quinazolinone ; synthesis
  • Is Part Of: Chemical papers, 2016-07, Vol.70 (7), p.983-993
  • Description: 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 1 H NMR, 13 C NMR, ESI-MS, IR and elemental analyses. The single crystal structure of 3-((5-((2-fluorobenzyl)thio)-4-phenyl-4 H -1,2,4-triazol-3-yl)methyl)quinazolin-4(3 H )-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)-4 H -1,2,4-triazol-3-yl)methyl)quinazolin-4(3 H )-one (VIIs) exhibited the best inhibitory effect against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri with the half-effective concentration (EC 50 ) 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-4 H -1,2,4-triazol-3-yl)methyl)quinazolin-4(3 H )-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.
  • Publisher: Cham: Springer International Publishing
  • Language: English;German;Russian;Slovak
  • Identifier: ISSN: 0366-6352
    EISSN: 1336-9075
    DOI: 10.1515/chempap-2016-0034
  • Source: AUTh Library subscriptions: ProQuest Central
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