Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors

Prenylation of Aromatic Secondary Metabolites: A New Frontier for Development of Novel Drugs

“…This study led to the discovery of a novel geranylgeranylated hydroxycoumarin (21) which exhibited 100 % preferential cytotoxicity against PANC-1 cells under nutrient-deprived medium at 6.25 µM making this compound a powerful new lead structure for the development of novel anticancer agents. In another related work conducted [19], O-prenylated derivatives involving farnesyloxy, geranyloxy and isopentenyloxy substituents at positions 3, 4, 5, 6, 7 and 8 of coumarin ring were synthesized and their lipoxygenase inhibitory activities together with the SAR studies were evaluated. The results obtained from these experiments showed that among the three groups of synthetic Oprenylated coumarins, farnesyloxy derivatives displayed the best inhibitory activity against soybean15-lipoxygenase (IC 50 : 1.7 to 5.8µm) while the isopentenyl derivatives displayed the least (IC 50 : 39.8 to 69.4 µM).…”

Crystal structure of 2-amino-3-cyano-7,7-dimethyl-5-oxo-4-(3,4,5-trifluorophenyl)-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C18H15F3N2O2

“…The interesting biological activity of these dihydropyrans made these compounds attractive targets in organic synthesis [6][7][8][9]. In the crystal structure of the title compound, the new formed pyran ring and the adjacent ketone ring are both basically planar, and the two planes are also essentially parallel each other.…”

Crystal structure of 2-amino-7,7-dimethyl-5-oxo-4-(3-phenoxy-phenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

“…The interesting biological activity of these dihydropyrans made these compounds attractive targets in organic synthesis [6][7][8][9].…”