Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety

Shi, Jun; Luo, Na; Ding, Muhan; Li, Chuanhui; Wan, Suran; Li, Peijia; Li, Junhong; Bao, Xiaoping

doi:10.6023/cjoc202007068

Cited by 6 publications

(3 citation statements)

References 17 publications

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“…Based on the aforementioned considerations and our long-term interest in the development of agricultural antimicrobial agents using the quinazoline-piperidine motif, ,− we envision that the integration of piperidine, hydrazide, and quinazoline structural units into a single molecule via active substructure splicing strategy , may help discover new efficient agricultural fungicides (Figure ). Herein, a series of new piperidine-4-carbohydrazide derivatives containing the quinazoline moiety are designed, synthesized, and assessed for their antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and Mechanism of Action of New Piperidine-4-carbohydrazide Derivatives Bearing a Quinazolinyl Moiety

Yang,

Liu,

Yan

et al. 2024

J. Agric. Food Chem.

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A series of new piperidine-4-carbohydrazide derivatives bearing a quinazolinyl moiety were prepared and evaluated for their fungicidal activities against agriculturally important fungi. Among these derivatives, the chemical structure of compound A45 was clearly verified by X-ray crystallographic analysis. The antifungal bioassays revealed that many compounds in this series possessed good to excellent inhibition effects toward the tested fungi. For example, compounds A13 and A41 had EC 50 values of 0.83 and 0.88 μg/mL against Rhizoctonia solani in vitro, respectively, superior to those of positive controls Chlorothalonil and Boscalid (1.64 and 0.96 μg/mL, respectively). Additionally, the above two compounds also exhibited notable inhibitory activities against Verticillium dahliae (with EC 50 values of 1.12 and 3.20 μg/mL, respectively), far better than the positive controls Carbendazim and Chlorothalonil (19.3 and 11.0 μg/mL, respectively). More importantly, compound A13 could potently inhibit the proliferation of R. solani in the potted rice plants, showing good in vivo curative and protective efficiencies of 76.9% and 76.6% at 200 μg/mL, respectively. Furthermore, compound A13 demonstrated an effective inhibition of succinate dehydrogenase (SDH) activity in vitro with an IC 50 value of 6.07 μM. Finally, the molecular docking study revealed that this compound could be well embedded into the active pocket of SDH via multiple noncovalent interactions, involving residues like SER39, ARG43, and GLY46.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and Mechanism of Action of New Piperidine-4-carbohydrazide Derivatives Bearing a Quinazolinyl Moiety

Yang,

Liu,

Yan

et al. 2024

J. Agric. Food Chem.

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“…Based on the aforementioned considerations and our previous studies [35][36][37][38][39] on the utilization of the quinazolinylpiperidine backbone to search for agricultural antimicrobial agents, we herein report the synthesis of a series of new quinazoline derivatives bearing both sulfonate ester group and piperidine-4-carboxamide moiety following the molecular hybridization strategy 40,41 (Fig. 2), and their antibacterial and antifungal properties against the phytopathogenic bacteria and fungi of agricultural relevance.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, crystal structure, and antimicrobial activities of new quinazoline derivatives containing both the sulfonate ester and piperidinylamide moieties

et al. 2023

Pest Management Science

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BACKGROUND To discover more efficient antimicrobial agents in agriculture, a series of new quinazoline derivatives bearing both sulfonate ester and piperidine‐4‐carboxamide moieties were synthesized and assessed for their antimicrobial effects. RESULTS All of the target compounds were fully characterized by proton (1H) nuclear magnetic resonance (NMR), carbon‐13 (13C) NMR, and high‐resolution mass spectroscopy (HRMS), and compound III‐6 containing a 3‐bromophenyl substituent was clearly confirmed via single‐crystal X‐ray diffraction analysis. The bioassay results indicated that some compounds displayed noticeable inhibitory effects in vitro against Xanthomonas oryzae pv. oryzicola (Xoc). Further measurements of median effective concentration (EC50) values showed that compound III‐17 bearing a 4‐methoxyphenyl group had the best anti‐Xoc efficacy (EC50 = 12.4 μg mL−1), far better than the commercialized bismerthiazol (77.5 μg mL−1). Moreover, this compound also demonstrated good protection and curative activities in vivo against rice bacterial leaf streak caused by Xoc. CONCLUSION Compound III‐17 had a good potential for further development as a new bactericide for controlling Xoc. © 2023 Society of Chemical Industry.

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“…Based on the above-mentioned considerations and our continuing interest in the development of anti-microbial agents using the quinazoline-piperidine backbone, ,,− we envisaged that a combination of the quinazoline backbone and the 2-aminothiazole heterocycle via the 4-piperidinylamide linker may be a feasible strategy , to discover new anti-microbial agents in agriculture (Figure ). Herein, a series of novel quinazoline-2-aminothiazole hybrids having a 4-piperidinylamide linker were rationally designed, facilely synthesized, and systematically evaluated for their in vitro and in vivo anti-microbial efficacies against ten fungi and three bacteria of agricultural importance.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Quinazoline-2-Aminothiazole Hybrids Containing a 4-Piperidinylamide Linker as Potential Fungicides against the Phytopathogenic Fungus Rhizoctonia solani

Ding

Lin

et al. 2022

J. Agric. Food Chem.

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A total of 29 novel quinazoline-2-aminothiazole hybrids containing a 4-piperidinylamide linker were designed, synthesized, and evaluated for their anti-microbial properties against phytopathogenic fungi and bacteria of agricultural importance. The anti-fungal assays indicated that some of the target compounds exhibited excellent inhibitory effects in vitro against Rhizoctonia solani. For example, 11 compounds within this series (including 4a, 4g, 4h, 4j, 4o, 4s, 4t, 4u, 4v, 4y, and 4b′) were found to possess EC50 values (effective concentration for 50% activity) ranging from 0.42 to 2.05 μg/mL against this pathogen. In particular, compound 4y with a 2-chloro-6-fluorophenyl substituent displayed a potent anti-R. solani efficacy with EC50 = 0.42 μg/mL, nearly threefold more effective than the commercialized fungicide Chlorothalonil (EC50 = 1.20 μg/mL) and also slightly superior to the other fungicide Carbendazim (EC50 = 0.53 μg/mL). Moreover, compound 4y could efficiently inhibit the growth of R. solani in vivo on the potted rice plants, displaying an impressive protection efficacy of 82.3% at 200 μg/mL, better than those of the fungicides Carbendazim (69.8%) and Chlorothalonil (48.9%). Finally, the mechanistic studies showed that compound 4y exerted its anti-fungal effects by altering the mycelial morphology, increasing the cell membrane permeability, and destroying the cell membrane integrity. On the other hand, some compounds demonstrated good anti-bacterial effects in vitro against Xanthomonas oryzae pv. oryzae (Xoo). Overall, the presented results implied that 4-piperidinylamide-bridged quinazoline-2-aminothiazole hybrids held the promise of acting as lead compounds for developing more efficient fungicides to control R. solani.

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Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety

Cited by 6 publications

References 17 publications

Design, Synthesis, Antifungal Activity, and Mechanism of Action of New Piperidine-4-carbohydrazide Derivatives Bearing a Quinazolinyl Moiety

Design, Synthesis, Antifungal Activity, and Mechanism of Action of New Piperidine-4-carbohydrazide Derivatives Bearing a Quinazolinyl Moiety

Design, synthesis, crystal structure, and antimicrobial activities of new quinazoline derivatives containing both the sulfonate ester and piperidinylamide moieties

Discovery of Novel Quinazoline-2-Aminothiazole Hybrids Containing a 4-Piperidinylamide Linker as Potential Fungicides against the Phytopathogenic Fungus Rhizoctonia solani

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