RESUMO
Breast cancer is probably the most prevalent cancer in women. The development of resistance to therapeutic agents and lack of targeted therapy for breast cancer cells provide motivation to identify new compounds for the treatment. With this objective in mind, a new series of 3-fluoro-4-methoxyphenyl group based 1,3,5-trisubstituted aryl-5-hydroxypyrazoline analogues 4a-l was synthesized through multi-step reaction sequence. The structures of the newly synthesized compounds were confirmed by IR, (1)H NMR, (13)C NMR, LC-MS and elemental analysis. They were screened for their in vitro anticancer and in vitro antioxidant activities. Among the tested compounds 4h, 4c and particularly 4i displayed promising cytotoxic effect on breast cancer cell lines. The compounds were also found to possess antioxidant activity when tested against DPPH free radical. Overall, this work has contributed to the development of promising leads for anticancer and antioxidant activities.
Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Antioxidantes/síntese química , Antioxidantes/farmacologia , Flúor/farmacologia , Pirazóis/farmacologia , Animais , Antineoplásicos/química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Chlorocebus aethiops , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Flúor/química , Radicais Livres/antagonistas & inibidores , Humanos , Células MCF-7 , Modelos Moleculares , Estrutura Molecular , Picratos/antagonistas & inibidores , Pirazóis/síntese química , Pirazóis/química , Relação Estrutura-Atividade , Células VeroRESUMO
In the present study, an efficient synthesis of some new substituted pyrazoline derivatives linked to a substituted pyrazole scaffold was performed by a multistep reaction sequences and compounds were screened for their anti-inflammatory, analgesic and antibacterial activities. The preliminary results revealed that the N-acylated (5e, 5h) and nitro substituted N-phenyl (6f) pyrazolyl-pyrazolines derivatives exhibited a very promising anti-inflammatory activity whereas 5h, 6f were interesting analgesic agents. The compounds with halo substituted phenyl group at C-3 of the pyrazoline ring (4a, 5g, 5h, 6a and 6b) were found to be active against clinical bacterial pathogens with MIC in the range of 0.2-0.4 mg/mL. Compound containing N-propionyl pyrazolyl-pyrazoline (5h) could be identified as the most active member within this study with a dual anti-inflammatory and antibacterial profile. Taken together, this study has led to the development of promising compounds.