Synthesis, Characterization and in vitro Anticancer Activity of Novel 8,4'-Oxyneolignan Analogues

• Published in: Journal of the Brazilian Chemical Society Vol. 28; no. 11; pp. 2229 - 2243
• Main Authors: Souza, Gisele C., Franchi, Gilberto C., Nowill, Alexandre E., Santos, Lourivaldo S., Alves, Claudio N., Barata, Lauro E. S., Andrade, Carlos K. Z.
• Format: Journal Article
• Language: English
• Published: SAO PAULO Soc Brasileira Quimica 01.11.2017; Sociedade Brasileira de Química
• Subjects: Chemistry; CHEMISTRY, MULTIDISCIPLINARY; Physical Sciences; Science & Technology; CELLS; ANTIFUNGAL ACTIVITY; TOXICITY; PIPER-REGNELLII; MTT assay; CANCER; antiproliferative activity; beta-ketoether; THERAPY; neolignans; ROOTS; beta-ketoester; LAURACEAE; MAGNOLIA-OFFICINALIS; β-ketoester; β-ketoether
• ISSN: 0103-5053; 1678-4790; 1678-4790
• DOI: 10.21577/0103-5053.20170075

Neolignans are a class of natural products with a wide range of biological effects. These substances are of great synthetic and biological interest, especially in searching for novel anticancer agents. In this paper, we report the synthesis of a new subclass of 8,4'-oxyneolignan analogues (beta-ketoethers and beta-ketoesters) and their cell viability assay on twenty four different cancer cells, among leukemias and carcinomas. Three compounds inhibited the growth of most human cancer cells. 2-Oxo-2-phenylethyl(2E)-3-[4-(2-oxo-2-phenylethoxy) phenyl] prop-2-enoate showed an antiproliferative activity superior to doxorubicin for U-87, U-138 MG and H1299 cell types and (E)-2-oxo-2-phenylethyl 3-(3-methoxy-4-(2-oxo-2-phenylethoxy) phenyl) acrylate was found to be very selective, demonstrating a growth inhibition of 92.0% against KG-1 cells. Furthermore, 1-oxo-1-phenylpropan-2-yl cinnamate exhibited significant inhibition activity in a range of 52.2 to 91.2% against twelve kinds of leukemia cell lines, revealing excellent results and very comparable to the reference drug.