Details

Autor(en) / Beteiligte

• Reis, Rúbia Castro Fernandes Melo
• Reis, Adriana Cotta Cardoso
• Torchelsen, Fernanda Karoline Vieira Silva
• de Lana, Marta
• Junior, Policarpo Ademar Sales
• Brandão, Geraldo Celio
• Braga, Saulo Fehelberg Pinto
• de Souza, Thiago Belarmino

Titel

Synthesis, trypanocidal and cytotoxic activities of α,β-unsaturated ketones derived from eugenol and analogues

Ist Teil von

• Medicinal chemistry research, 2022-12, Vol.31 (12), p.2152-2159

Ort / Verlag

New York: Springer US

Erscheinungsjahr

2022

Quelle

SpringerNature Journals

Beschreibungen/Notizen

• This work describes the synthesis, structural characterization, trypanocide and cytotoxic evaluation of α,β-unsaturated ketones derived from eugenol and analogues. Among the synthesized compounds, the cyclopentanonic/dihydroeugenol derivative 12 was active against amastigote forms of Trypanosoma cruzi at 5.2 nM (700 times more potent than benznidazole) and represents a potential hit for future structural optimizations to reduce its toxicity. All the compounds were also evaluated against a healthy human and four cancer cell lines and the derivative 10 was more active than doxorubicin against three cancer cells (IC 50 values between 2.03–23.51 µM) and showed the higher selectivity index considering the human cells. Derivative 14 was also more potent and selective than doxorubicin against two cancer cells (IC 50 values between 4.71–8.86 µM). Graphical abstract