Synthesis,in vitro antibacterial and antifungal evaluation of novel 1,3,4-oxadiazole thioether derivatives bearing the 6-fluoroquinazolinylpiperidinyl moiety  

作　　者：Jun Shi Na Luo Muhan Ding Xiaoping Bao 

机构地区：[1]State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering,Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education,Center for Research and Development of Fine Chemicals,Guizhou University,Guiyang 550025,China

出　　处：《Chinese Chemical Letters》2020年第2期434-438,共5页中国化学快报（英文版）

基　　金：financially supported by Young Top-Notch Talent Support Program of Guizhou Provincial Education Department(No.2018038);Guizhou Provincial High-Level Overseas Talents Innovation and Enterpreneurship Program(No.201809);Breeding Program of Guizhou University(No.20185781)。

摘　　要：A series of structurally novel 1,3,4-oxadiazole thioether derivatives(6a-6z) containing a 6-fluoroquinazolinylpiperidinyl moiety were designed and synthesized using pharmacophore hybrid approach,and their structures were fully characterized by ^1H NMR,^(13)C NMR and HRMS spectra.Among them,the structure of compound 6 d was further corroborated via single-crystal X-ray diffraction analysis.In vitro antibacterial bioassays showed that compounds 6 a,6 g,6 u and 6 v possessed EC_(50) values of 30.4,30.6,27.5 and 26.0 μg/mL against phytopathogenic bacterium Xanthomonas oryzae pv.oryzae,respectively,which were significantly superior to that of commercially-available bactericide Bismerthiazol(85.1 μg/mL).Moreover,in vitro antifungal bioassays indicated that seven compounds demonstrated broad-spectrum fungicidal acitivties against six types of phytopathogenic fungi at 50 μg/mL.The present work showed the potential of 1,3,4-oxadiazole thioether derivatives carrying a 6-fluoroquinazolinylpiperidinyl moiety as effective antimicrobial agents for crop protection,deserving further investigations in the future.A series of structurally novel 1,3,4-oxadiazole thioether derivatives（6a-6z） containing a 6-fluoroquinazolinylpiperidinyl moiety were designed and synthesized using pharmacophore hybrid approach,and their structures were fully characterized by 1H NMR,13C NMR and HRMS spectra.Among them,the structure of compound 6 d was further corroborated via single-crystal X-ray diffraction analysis.In vitro antibacterial bioassays showed that compounds 6 a,6 g,6 u and 6 v possessed EC50 values of 30.4,30.6,27.5 and 26.0 μg/mL against phytopathogenic bacterium Xanthomonas oryzae pv.oryzae,respectively,which were significantly superior to that of commercially-available bactericide Bismerthiazol（85.1 μg/mL）.Moreover,in vitro antifungal bioassays indicated that seven compounds demonstrated broad-spectrum fungicidal acitivties against six types of phytopathogenic fungi at 50 μg/mL.The present work showed the potential of 1,3,4-oxadiazole thioether derivatives carrying a 6-fluoroquinazolinylpiperidinyl moiety as effective antimicrobial agents for crop protection,deserving further investigations in the future.

关 键 词：1 3 4-OXADIAZOLE THIOETHER Fluoroquinazolinylpiperidinyl SYNTHESIS Antibacterial ACTIVITY ANTIFUNGAL ACTIVITY 

分 类 号：O626[理学—有机化学] TQ455[理学—化学]