New 5-carba-pterocarpans: Synthesis and preliminary antiproliferative activity on a panel of human cancer cells.

Francisco V Gaspar, Soraya Marques Ribeiro, Júlio C F Barcellos, Samuel Monteiro, Jorge L O Domingos, Maria Claudia Dos Santos Luciano, Carlos R K Paier, Cláudia Pessoa, Paulo R R Costa

Bioorganic chemistry 2021 Feb

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Natural pterocarpans and synthetic 5-carba-pterocarpans are isosteres in which the oxygen atom at position 5 in the pyran-ring of pterocarpans is replaced by a methylene group. These 5-carba-analogues were obtained in good yields through the palladium-catalyzed oxyarylation of alcoxy-1,2-dihydronaphthalens with o-iodophenols in PEG-400. They were evaluated on human cancer cell lineages derived respectively from prostate tumor (PC3, IC50 = 11.84 μmol L-1, SI > 12)) and acute myeloid leukemia (HL-60, IC50 = 8.81 μmol L-1, SI > 16), highly incident cancer types presenting resistance against traditional chemotherapeutics. Compound 6c (LQB-492) was the most potent (IC50 = 3.85 μmol L-1, SI > 37) in SF-295 cell lineage (glioblastoma). Such findings suggest that 5-carba-pterocarpan can potentially be new hit compounds for further development of novel antiproliferative agents. Copyright © 2021 Elsevier Inc. All rights reserved.

Citation

Francisco V Gaspar, Soraya Marques Ribeiro, Júlio C F Barcellos, Samuel Monteiro, Jorge L O Domingos, Maria Claudia Dos Santos Luciano, Carlos R K Paier, Cláudia Pessoa, Paulo R R Costa. New 5-carba-pterocarpans: Synthesis and preliminary antiproliferative activity on a panel of human cancer cells. Bioorganic chemistry. 2021 Feb;107:104584