Agroquímica

URI Permanente desta comunidade

http://repositorio.ufes.br/handle/10/17376
Programa de Pós-Graduação em Agroquímica

Centro: CCENS
Telefone: (28) 3552 8731
URL do programa: http://www.agroquimica.alegre.ufes.br/pos-graduacao/PPGAQ

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Navegando Agroquímica por Assunto "Adamantano"

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    Avaliação do efeito antifúngico de derivados triazólicos obtidos por estratégia de hibridação molecular
    (Universidade Federal do Espírito Santo, 2024-04-02) Silva, Jéssica Adalgisa Barbosa; Morais, Pedro Alves Bezerra ; https://orcid.org/0000-0001-5501-7350; http://lattes.cnpq.br/5220285635137407; https://orcid.org/0000-0003-1044-7001; http://lattes.cnpq.br/7079506819678915; Campos, Othon Souto ; https://orcid.org/0000-0002-8285-0898; http://lattes.cnpq.br/4021571191714416; Paula, Heberth de ; https://orcid.org/0000-0001-6197-4165; http://lattes.cnpq.br/0823599580312700
    Black pepper has been increasingly gaining ground in the international market, accounting for 98% of Brazilian pepper exports. Espírito Santo is the most prominent state in Brazil as a black pepper producer, contributing 60% of the country's production of this spice. However, this cultivation is frequently threatened by the fungus Fusarium solani, which causes root rot in the plants. With the aim of producing new promising molecules against this pathogen, novel triazole compounds derived from natural products were synthesized. Initially, the azido-adamantane derivatives 20 and 23 were obtained and subsequently combined with alkynes derived from natural products, such as isatin, p-coumaric acid, eugenol, and thymol, to form the 1,4-disubstituted 1,2,3- triazole ring. Therefore, in this study, six molecular hybrids were designed through the copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC), also known as "Click Chemistry," in the presence of copper(II) sulfate pentahydrate and sodium ascorbate. The compounds 25a-b and 26a-d were characterized by 1H NMR, 13C, COSY, HMQC, HSQC, and infrared spectroscopy (FTIR) and achieved yields ranging from 20.35% to 63.66%. Molecular docking studies between the synthesized compounds and the enzyme Succinate Dehydrogenase (SDH), PDB: 1NEN, indicated that compounds 26b and 26d are potential SDH inhibitors, with hydrogen bond interactions analogous to those of the original ligand DNT, involving the amino acid residues TYR83, TRP164, and ARG31.
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    Sintese de derivados triazólicos do adamantano com potencial atividade fungicida frente a Fusarium solani f. sp. Piperis
    (Universidade Federal do Espírito Santo, 2024-04-01) Ferreira, Lara Chaves de Freitas; Morais, Pedro Alves Bezerra ; https://orcid.org/0000-0001-5501-7350; http://lattes.cnpq.br/5220285635137407; https://orcid.org/0000-0002-0021-3810; http://lattes.cnpq.br/6358247933891084; Campos, Othon Souto ; https://orcid.org/0000-0002-8285-0898; http://lattes.cnpq.br/4021571191714416; Paula, Heberth de ; https://orcid.org/0000-0001-6197-4165; http://lattes.cnpq.br/0823599580312700
    Black pepper is a spice widely used since antiquity and is considered a valuable product for the agribusiness industry. The state of Espírito Santo is the largest producer of black pepper in Brazil, thus holding significant importance in the national economic scenario. However, black pepper cultivars suffer from large-scale fungal infections, with Fusarium solani being one of the main contributors to the reduced lifespan of black pepper plants. In the quest for discovering new, more effective molecules against fungal diseases, understanding their modes of action is crucial. Commercially available agrochemicals can inhibit fungal growth by inhibiting the enzyme succinate dehydrogenase, which is vital for the electron transport chain. Compounds containing the 1,2,3-triazole or adamantane nucleus exhibit numerous biological activities, including antifungal properties. The 1,2,3- triazole ring is solely obtained through synthetic means, commonly synthesized via copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), following the "click chemistry" strategy. Accordingly, eight new adamantane-derived triazoles, 32a-c and 33a-e, were synthesized for evaluation of their activity against F. solani. Additionally, potential interactions of the new triazoles with the succinate dehydrogenase enzyme were assessed through molecular docking studies. The compounds interacted with the ubiquinone binding site of SDH through various hydrogen bonds, hydrophobic interactions, and π-stacking interactions, with 33e being the best compound in terms of interaction with the enzyme. It formed hydrogen bonds with the same amino acid residues as DNT, the original ligand of PBD 1NEN. The structures of the triazoles have been elucidated so far by 1H, 13C NMR, HSQC, HMBC, COSY, and Infrared spectroscopy, and subsequent mass spectrometry analyses will be conducted