One-pot synthesis and antifungal activity against plant pathogens of quinazolinone derivatives containing an amide moiety

Zhang, Jin; Liu, Jia; Ma, Yangmin; Ren, Decheng; Cheng, Pei; Zhao, Jiawen; Zhang, Fan; Yao, Yuan

doi:10.1016/j.bmcl.2016.03.052

Cited by 80 publications

(36 citation statements)

References 41 publications

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“…Strikingly, Zhang et al . verified the antifungal mechanism of 3‐acylaminoquinazolinone derivatives as chitinase inhibitors, and found a carbonyl group at the N ‐3 position of quinazolin‐4(3 H )‐one nucleus plays a key role in inhibiting chitinous biosynthesis …”

Section: Introductionmentioning

confidence: 79%

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Wang

Yan

et al. 2018

ChemistrySelect

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A series of quinazolin‐4(3H)‐one derivatives containing a hydrazide moiety were designed, synthesized and characterized in detail via FT‐IR, 1H NMR, 13C NMR and HRMS spectra. The antifungal activities against Rhizoctonia solani (Rs) and Fusarium graminearum (Fg) were evaluated in vitro. The bioassay results indicated that most of the title compounds exhibited significant antifungal activities against Rs and Fg. Strikingly, the EC50 values of some title compounds against Rs are obviously superior to that of the positive control carbendazim. Based on the antifungal bioassay results against Rs, the comparative molecular filed analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were generated to investigate the structure‐activity relationship of title compounds against Rs. The analytical results indicated that these two models exhibited good predictive accuracies and could provide significant structural insights for the design of bioactive quinazolin‐4(3H)‐one derivatives containing a hydrazide moiety.

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Section: Introductionmentioning

confidence: 79%

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Wang

Yan

et al. 2018

ChemistrySelect

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“…Introduction of substituents together with their specific positions in the aromatic ring determines whether they behave as antioxidants, cytotoxic, or mutagenic agents . While the 2‐substituted quinazolinones have antifungal and antihyperlipidemic activities, 2,3‐disubstituted quinazolinones possess anticancer, anticonvulsant, antimicrobial, and anti‐inflammatory activities …”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 2,3‐disubstituted quinazolin‐4(3H)‐one derivatives containing hydrazone skeleton as potent urease inhibitors and their antimicrobial activities

Akyüz

Beriş

Kahveci

et al. 2019

Journal of Heterocyclic Chem

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A new series of quinazolinones containing hydrazone moiety were synthesized, and their inhibitory activities on urease were assessed in vitro. Most of the compounds exhibited potent urease inhibitory activity. Among the synthesized compounds, molecule 4a bearing furan ring has the best inhibitory effect against urease with IC50 = 2.90 ± 0.11 μg/mL. Compounds 4f, 4g, 4h, 4i, and 4j have hydroxy group on phenyl ring. Compound 4i is the most active inhibitor among these compounds with IC50 = 5.01 ± 0.10 μg/mL, which has 3‐Cl and 4‐Br on phenyl ring. Also, newly synthesized compounds had been tested for their antimicrobial effects against three of Gram‐positive bacteria (Bacillus cereus 702 Roma, Staphylococcus aureus ATCC 25923, and Streptococcus pyogenes ATCC 19615) and three of Gram‐negative bacteria (Escherichia coli ATCC 25922, Proteus vulgaris ATCC 13315, and Pseudomonas aeruginosa ATCC 27853). Antimicrobial activity results show that compounds 4a, 4h, 4j, 4f, and 4l have the lowest minimum inhibitory concentration (MIC) value of 1000 μg/mL to all tested bacteria. The other compounds have the MIC value of >1000 μg/mL to all tested bacteria.

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“…22 The high mortality factor of hypertension and serious side effects of the clinically known drugs dimensioned their applications, directed the research efforts for developing novel effective hits/leads. The recent publications describing diverse biological properties of quinazoline containingcompounds as antibacterial, 23 antiviral, 24 antifungal, 25 antiplasmodial, 26 anti-inammatory, 27 cholinesterase, 28,29 and monoamine oxidase inhibitors 30 also prompted the present work.…”

Section: Introductionmentioning

confidence: 99%

“…Found: C, 67.38; H, 6.30; N, 12.42.4-Hydroxy-3-phenyl-4-(pyrrolidine-1-carbonyl)-3,4-dihydroquinazolin-2(1H)-one (13b). It was obtained from the reaction of 10a and 11b (reaction time 10 h) as colorless microcrystals from methanol with mp 184-186 C and yield 74% (1 25. g).…”

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confidence: 99%

Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

et al. 2019

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One-pot synthesis and antifungal activity against plant pathogens of quinazolinone derivatives containing an amide moiety

Cited by 80 publications

References 41 publications

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Synthesis of novel 2,3‐disubstituted quinazolin‐4(3H)‐one derivatives containing hydrazone skeleton as potent urease inhibitors and their antimicrobial activities

Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

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