Citation: Shi Jun, Luo Na, Ding Muhan, Bao Xiaoping. Synthesis, in vitro antibacterial and antifungal evaluation of novel 1, 3, 4-oxadiazole thioether derivatives bearing the 6-fluoroquinazolinylpiperidinyl moiety[J]. Chinese Chemical Letters, ;2020, 31(2): 434-438. doi: 10.1016/j.cclet.2019.06.037 shu

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

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

baoxp_1980@aliyun.com

Received Date: 14 May 2019
Revised Date: 15 June 2019
Accepted Date: 19 June 2019
Available Online: 20 June 2019

Figures(4)

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 6d was further corroborated via single-crystal X-ray diffraction analysis. In vitro antibacterial bioassays showed that compounds 6a, 6g, 6u and 6v 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.
- 1, 3, 4-Oxadiazole thioether,
- Fluoroquinazolinylpiperidinyl,
- Synthesis,
- Antibacterial activity,
- Antifungal activity
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