Synthesis of Eugenol-Fluorinated Triazole Derivatives and Evaluation of Their Fungicidal Activity

Lima, Ângela; Paula, Wenderson de; Leite, Iris Carolina Henrique de Lima; Gazolla, Poliana; Abreu, Lucas M.; Fonseca, Victor R.; Romão, Wanderson; Lacerda, Valdemar; Queiroz, Vagner de; Teixeira, Róbson Ricardo; Costa, Adílson Vidal

doi:10.21577/0103-5053.20220040

Cited by 3 publications

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“…Its derivatives exhibit leishmanicidal, insecticidal, anti-inflammatory, antibacterial, antioxidant properties. Notably, extensive chemical modification of eugenol has resulted in substances with antifungal activity. − …”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Almeida lima,

Moreira,

Gazolla

et al. 2024

J. Agric. Food Chem.

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A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper(I)-catalyzed azide–alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. Triazoles 2k, 2m, 2l, and 2n, at 100 ppm, were the most effective, reducing mycelial growth by 88.3, 85.5, 82.4, and 81.4%, respectively. Molecular docking calculations allowed us to elucidate the binding mode of these derivatives in the catalytic pocket of C. gloeosporioides CYP51. The best-docked compounds bind closely to the heme cofactor and within the channel access of the lanosterol (LAN) substrate, with crucial interactions involving residues Tyr102, Ile355, Met485, and Phe486. From such studies, the antifungal activity is likely attributed to the prevention of substrate LAN entry by the 1,2,3-triazole derivatives. The triazoles derived from natural eugenol represent a novel lead in the search for environmentally safe agents for controlling C. gloeosporioides.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Almeida lima,

Moreira,

Gazolla

et al. 2024

J. Agric. Food Chem.

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“…Moreover, the 1,2,3-triazole nucleus can act as a pharmacophoric group, that is, the portion of the substance responsible for its biological activity. Thus, 1,2,3-triazole fragments have been introduced into the skeleton of numerous molecules, resulting in the discovery of compounds with important biological activities. − For example, the connection of 1,2,3-triazole and glycerol fragments resulted in triazole derivatives with significant fungicidal activity against Colletotrichum gloeosporioides. These derivatives showed efficacy compared to the commercial fungicide tebuconazole. , …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Lima

Teixeira

Moraes

et al. 2023

J. Agric. Food Chem.

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In agriculture, the control of fungal infections is essential to improve crop quality and productivity. This study describes the preparation and fungicidal activity evaluation of 12 glycerol derivatives bearing 1,2,3-triazole fragments. The derivatives were prepared from glycerol in four steps. The key step corresponded to the Cu(I)-catalyzed alkyne−azide cycloaddition (CuAAC) click reaction between the azide 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes (57−91% yield). The compounds were characterized by infrared spectroscopy, nuclear magnetic resonance ( 1 H and 13 C), and high-resolution mass spectrometry. The in vitro assessment of the compounds on Asperisporium caricae, that is, the etiological agent of papaya black spot, at 750 mg L −1 showed that the glycerol derivatives significantly inhibited conidial germination with different degrees of efficacy. The most active compound 4-(3-chlorophenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl) methyl)-1H-1,2,3-triazole (4c) presented a 91.92% inhibition. In vivo assays revealed that 4c reduced the final severity (70.7%) and area under the disease severity progress curve of black spots on papaya fruits 10 days after inoculation. The glycerol-bearing 1,2,3-triazole derivatives also present agrochemicallikeness properties. Our in silico study using molecular docking calculations show that all triazole derivatives bind favorably to the sterol 14α-demethylase (CYP51) active site at the same region of the substrate lanosterol (LAN) and fungicide propiconazole (PRO). Thus, the mechanism of action of the compounds 4a−4l may be the same as the fungicide PRO, blocking the entrance/ approximation of the LAN into the CYP51 active site by steric effects. The reported results point to the fact that the glycerol derivatives may represent a scaffold to be explored for the development of new chemical agents to control papaya black spot.

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Implications of Active Intermediate and Olefin Attachment Position in the Piperine Metathesis

França,

da Silva,

Lima-Neto

et al. 2023

Kinet Catal

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Synthesis of Eugenol-Fluorinated Triazole Derivatives and Evaluation of Their Fungicidal Activity

Cited by 3 publications

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Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Implications of Active Intermediate and Olefin Attachment Position in the Piperine Metathesis

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