Antitumor and antileishmanial activities of limonene-thiosemicarbazones bearing heterocycles nucleous

• Autor(a) principal: Vandresen, Fabio
• Data de Publicação: 2022
• Outros Autores: Almeida-Batista , Sabrina Alencar de, Caldeira, Maria Eduarda Bueno, Romeral, Richard de Albuquerque Felizola, Nakamura, Celso Vataru, Ruiz, Ana Lucia Tasca Góes, Silva, Cleuza Conceição da
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Research, Society and Development
• Texto Completo: https://rsdjournal.org/index.php/rsd/article/view/28152
• topic: Limoneno; Tiossemicarbazonas; Imidazol; Atividade antitumoral.; Limoneno; Tiosemicarbazona; Imidazol; Actividad antitumoral.; Limonene; Thiosemicarbazone; Imidazole; Antitumor activity.

In the present study, we provided the synthesis of a series of R-(+)- and S-(-)-limonene-based thiosemicarbazones containing different pentacyclic heterocyclic nucleus moiety focused in the search of novel antitumor and antileishmanial agents. In the antitumor assay, the derivative imidazole of S-(-)-limonene 8 was the most active compound, especially for U-251, UACC-62 and K562 human tumor cell lines with GI50 ranging from 1.0 to <0.25 µg.mL-1. On the other hand, the imidazole-thiosemicarbazone of R-(+)-limonene 4 was the most promising derivative against the promastigote form of L. amazonensis (IC50=5.9µM). Meanwhile, thiosemicarbazones without limonene moiety (9-12) showed the lowest activities in the biological assays performed. The results demonstrated the influence of the lipophilic molecular character and stereochemistry of chiral monoterpene on the evaluated activities.