Derivados triazólicos de isatina como potenciais agentes herbicidas

• Autor(a) principal: Britto, Karolinni Bianchi
• Data de Publicação: 2019
• Tipo de documento: Dissertação
• Idioma: por
• Título da fonte: Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)
• Texto Completo: http://repositorio.ufes.br/handle/10/10945
• topic: Isatin; 1,2,3-Triazoles; Cu (I) catalyzed azido-alkine cycloaddition; Herbicide activity; Isatina; 1,2,3-Triazóis; Click chemistry; CuAAC; Cicloadição azido-alcino catalisada por Cu(I); Atividade herbicida; Herbicidas; Química; Química farmacêutica; Farmácia; 615.1

Isatin (1H-indole-2,3-dione) is an important indole-type heterocycle found in plants, animals, fungi and also in humans. Studies have shown that isatin, as well as its derivatives, have a broad spectrum of activity, including herbicidal activity. The triazole ring is also of great relevance for medicinal chemistry because it acts not only as a pharmacophoric group but also acts as a bridge between biomolecules of interest for the formation of hybrids and also works to improve the pharmacological and pharmacokinetic properties of the drugs. Considering the importance of isatin and triazoles, known in the literature for various activities, the work was directed to the synthesis of isatin hybrids by the preparation of new isatin-N-1 substituted triazole derivatives via the click chemistry strategy by azido cycloaddition (CuAAC), preparation of isatin derivatives by N-alkylation, as well as in vivo evaluation, by germination test and initial development against lettuce (Lactuca sativa) and onion (Allium cepa). NMR 1H and 13C, HSQC, HMBC, COSY, IR and HRESIMS analyzes confirmed the achievement of all compounds. For the herbicidal assay, the synthesized compounds were diluted in 0.1% DMSO solutions at the concentration of 100 mg.L-1 and tested for both seeds. The evaluated variables were percentage of germination, germination speed index, shoot length, root length and fresh mass. Eighteen compounds were synthesized, of which thirteen are unpublished in the literature. As regards the activity of isatin derivatives, it is noted that there is an effect on the initial development and growth of the seedlings, demonstrated by the inhibition of lettuce shoot length and onion root length evaluated mainly by compounds 65 and 71, respectively. Thus, some evaluated compounds exhibited properties suggesting their potential utility as herbicides; however, further and further tests are necessary for this action to be proven, as well as for the structural optimization of these derivatives towards the discovery of new, more potent inhibitors, in view of the emergence of weeds resistant to currently available inhibitors