Synthesis of novel quinazolin-4(3H)-one derivatives containing the 7-oxo-1,2,4-triazolo[1,5-a]pyrimidine moiety as effective agricultural bactericides against the pathogen Xanthomonas oryzae pv. oryzae

Du, Huan; Fan, Zhijiang; Yang, Lan; Bao, Xiaoping

doi:10.1007/s11030-017-9782-3

Cited by 13 publications

(7 citation statements)

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“…Triazole derivatives have attracted considerable interest in the scientific community due to their vast range of biological activities. In addition to antifungal action [ 14 , 15 , 16 , 17 , 18 , 19 ], they were shown to possess other antimicrobial effects such as antibacterial, including anti-tuberculous activity [ 20 , 21 , 22 , 23 , 24 ], antiparasitic [ 25 , 26 , 27 ] and anti-HIV effects [ 28 ] as well as anticholinesterase [ 29 ], antiangiogenic [ 30 ], anticancer [ 31 , 32 ], antidiabetic [ 33 , 34 ] and anticonvulsant activities [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols (3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and the evaluation of their antifungal activity. In silico prediction of biological activity spectra with computer program PASS indicate that the compounds have a high novelty compared to the known antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k, followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8 µM, respectively. Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular docking studies on C. albicans sterol 14α-demethylase (CYP51) and DNA topoisomerase IV were used to predict the mechanism of antifungal activities. According to the docking results, the inhibition of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We also showed that most active compounds have a low cytotoxicity, which allows us to consider them promising antifungal agents for the subsequent testing activity in in vivo assays.

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Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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“…Appearing fine effects on antimalarial, antifungal, anti‐obesity, anticancer, antibacterial, anti‐flammatory, insecticidal and vasorelaxant activities, natural quinazolin‐4(3 H )‐ones show important applications and development perspectives in searching for bioactive lead compounds . Further investigations on the structural optimization of quinazolin‐4(3 H )‐ones found that introducing Schiff base, amide, 1,2,4‐triazole,, 1,2,4‐triazolo[3,4‐ b ][1,3,4]thiadiazole and 1,2,4‐triazolo[1,5‐ a ]pyrimidine scaffolds at the N ‐3 position of quinazolin‐4(3 H )‐one could greatly enhance and broaden their antimicrobial activities. Strikingly, Zhang et al .…”

Section: Introductionmentioning

confidence: 99%

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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“…Moreover, this class of compounds did not display inhibition activity against three fungi tested. The above findings indicated that quinazolin-4-one derivatives containing the 7-oxo-1,2,4-triazolo [1,5-a]pyrimidine moiety have a potential as promising candidates for the development of new and more efficient agricultural bactericides 14 .…”

Section: Triazol Derivativesmentioning

confidence: 88%

A review of compounds derivatives with antimicrobial activities

Thangabalan¹,

Mahesh²

2023

World J. Bio. Pharm. Health Sci.

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Antimicrobial resistance represents a serious threat to human health across the globe. The cost of bringing a new antibiotic from discovery to market is high and return on investment is low. Furthermore, the development of new antibiotics has slowed dramatically since the 1950s’ golden age of discovery. Medicinal compounds synthesis produce a variety of bioactive compounds that could be used to build a new way for the future discovery pipeline. While many studies have focused on specific aspects of synthetic compounds with antibacterial properties, a comprehensive review of the antibacterial potential of compounds has never before been attempted. This review aims to evaluate reports on some derivatives with significant antimicrobial activities.

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Synthesis of novel quinazolin-4(3H)-one derivatives containing the 7-oxo-1,2,4-triazolo[1,5-a]pyrimidine moiety as effective agricultural bactericides against the pathogen Xanthomonas oryzae pv. oryzae

Cited by 13 publications

References 28 publications

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

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

A review of compounds derivatives with antimicrobial activities

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