Synthesis and cytotoxic activity of some 3-benzyl-5-arylidenefuran-2(5H)-ones.
3-Benzyl-furan-2(5H)-one (2a) and 3-(4-bromobenzyl)-furan-2(5H)-one (2b) were treated with TBDMSOTf and converted into the corresponding tert-butyldimethyl-silylfuran ethers. These furans were further condensed with several aromatic aldehydes affording compounds 5-14 with general 3-benzyl-5-arylidene-furan-2(5H)-one structures in 31% to 98% yields. Such compounds are analogues of the naturally occurring nostoclide lactones, reported to present moderate cytotoxic activity. Compounds 5-14 were submitted to an in vitro bioassay against the HL-60, HCT-8, SF295 and MDA-MB-435 cancer cell lines using the MTT cytotoxicity assay.
Teixeira
Róbson Ricardo
RR
Department of Chemistry, Federal University of Viçosa, Av. P.H. Rolfs, S/N, CEP 36570-000, Viçosa, MG, Brazil.
Barbosa
Luiz Cláudio
LC
Maltha
Célia Regina Alvares
CR
Rocha
Marcelo Eça
ME
Bezerra
Daniel Pereira
DP
Costa-Lotuf
Letícia Veras
LV
Pessoa
Cláudia
C
Moraes
Manoel Odorico
MO
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared
D000970:Antineoplastic Agents; D005663:Furans