A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity

AUTOR(ES)

Santos, Iara S.

FONTE

J. Braz. Chem. Soc.

DATA DE PUBLICAÇÃO

2019-01

RESUMO

Novel isatinspirooxazine derivatives were designed and synthesized as potential anti-proliferative agents. The new compounds were obtained from aldol condensation reactions between isatin and 3-(hydroxyimino)butan-2-one in the presence of an organic base in order to generate an aldol adduct, followed by cyclization in trifluoroacetic acid, providing the desired isatinspirooxazines in 30 to 80% yield. All the synthesized compounds, including the starting material and the synthetic intermediates, were tested for in vitro anti-proliferative activity against cell lines MCF-7 and MDA-MB231 (breast cancer) and A549 (lung cancer), highlighting the compound 4-methyl,5'-methyl-spiro[(5-aza-4-eno-3-one-cyclohexane)-1,3'-(1H-indol-one)] with an IC50 (half maximal inhibitory concentration) = 0.34 µM, more potent than the reference drug, doxorubicin (IC50 = 1.88 µM), in breast cancer line MDA-MB231.

Documentos Relacionados

• In vitro anti-proliferative and apoptotic activity of different fractions of Artemisia armeniaca
• Production of a novel probiotic date juice with anti-proliferative activity against Hep-2 cancer cells
• Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
• Mutation of the casein kinase II phosphorylation site abolishes the anti-proliferative activity of p53.
• Phenolic composition, antioxidant and anti-proliferative activities of edible and medicinal plants from the Peruvian Amazon