Synthesis and antiproliferative activity of C-3 functionalized isobenzofuran-1(3H)-ones

A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. Th...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-02, Vol.18 (2), p.1881-1896
Main Authors: Teixeira, Róbson Ricardo, Bressan, Gustavo Costa, Pereira, Wagner Luiz, Ferreira, Joana Gasperazzo, de Oliveira, Fabrício Marques, Thomaz, Deborah Campos
Format: Article
Language:English
Subjects:
antiproliferative activity
Benzofurans - chemical synthesis
Benzofurans - chemistry
Benzofurans - pharmacology
Benzofurans - toxicity
Cell Proliferation - drug effects
Cell Survival - drug effects
Computer Simulation
Cytotoxicity
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Etoposide - pharmacology
Humans
Inhibitory Concentration 50
isobenzofuran-1(3H)-one
K562 Cells
Leukemia
Magnetic Resonance Spectroscopy
phtalides
Structure-Activity Relationship
U937 Cells
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Summary:A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules18021881