Design and synthesis of new derivatives of 3-acetylcoumarin as 15-lipoxygenase inhibitors

15-Lipoxygenase (15-LOX) is one of the most important enzyme of lipoxygenase family in animals and plants. The critical role of the enzyme in creating human disease such as inflammatory disease of the respiratory system, sensitivity and also prostate cancer has been demonstrated.2 In this research, with design and synthesis acetylcoumarin derivatives, we intend to evaluate their inhibitory potency against soybean 15-lipoxygenase. Herein, we report that new derivatives of compound 2 were synthesized through Knoevenagel condition of desired dihydroxybenzaldehyde 1 with ethyl acetoacetate. Then all of the O-prenylated 3- acetylcoumarins 3 were synthesized by hydroxyl3-acetyl coumarin with the desired prenyl bromide in presence of sodium hydride in DMF and their tension of inhibition are surveyed on soybean 15-lipoxygenase. In the following, these mentioned compounds were compared with prenyled coumarin derivatives in terms of inhibitory activity against on soybean 15-lipoxygenase enzyme.3 All synthesized compounds structures were determined on the basis of their mass spectrum, 1H and 13C NMR and IR spectroscopic data.

کلیدواژه ها:

Synthesis ، inhibitors ، 15-lipoxygenase ، Knoevenagel condensation ، alkylation