NEW SYNTHETIC HYDROXYLATED BIPHENYL CHALCONES, A POTENTIAL BIOACTIVE AGENTS FROM NATURAL SOURCES

1,3-Diaryl-2-propen-1-ones, commonly known as chalcones, have displayed remarkable variety of biological activities, among which anti-malarial, anti-inflammatory, immunomodulatory and antitumoral1. This class of anticancer agents have shown promising therapeutic efficacy for the management of human cancers. Chalcones, considered as precursors of flavonoids and isoflavonoids, are abundant in edible plants. In our laboratory we are actively engaged in the synthesis and biological evaluation (e.g. anti-malignant melanoma cancer) of hydroxylated natural-like biphenyls2. Hydroxylated biphenyl unit is embedded in many structures of bioactive natural products and some of them are present in compounds of high biological relevance. Compared to 2-methoxy phenols, 3,3'-dimethoxy-2,2'-dihydroxy-biphenyls generally manifest higher activity and less toxicity than the corresponding monomers. It is also known that the presence of a prenylated or unsaturated alkyl chain on flavonoids and chalcones, can lead to a remarkable increase in bioactivity3. We herein report the synthesis, by Claisen-Schmidt condensation reaction base catalysed, of novel C2-symmetry hydroxylated (Type A and B) and prenylated chalcones based on a biphenyl scaffold and their corresponding monomers. References: 1)Sharma, A. et al. Biorg. & Med. Chem. 2010, 18, 4711-4720. 2)Pisano, M. et al. BMC Cancer, 2016, 16(1):317 3)Tatsuzaki, J. et al. J Nat. Prod. 2006, 69, 1445-1449.