Open AccessAntitumor and antileishmanial activities of limonene-thiosemicarbazones bearing heterocycles nucleous
Author(s) -
Fábio Vandresen,
Sabrina Alencar de Almeida-Batista,
Maria Eduarda Bueno Caldeira,
Richard de Albuquerque Felizola Romeral,
Celso Vataru Nakamura,
Ana Lúcia Tasca Góis Ruiz,
Cleuza Conceição da Silva
Publication year - 2022
Publication title -
research, society and development
Language(s) - English
Resource type - Journals
ISSN - 2525-3409
DOI - 10.33448/rsd-v11i5.28152
Subject(s) - imidazole , limonene , moiety , chemistry , stereochemistry , semicarbazone , derivative (finance) , monoterpene , combinatorial chemistry , organic chemistry , essential oil , chromatography , financial economics , economics
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.