Synthesis and evaluation of anticancer activity of 6-pyrazolinylcoumarin derivatives

Abstract

A series of novel 6-pyrazolinylcoumarins has been synthesized via multi-step protocol. The synthetic procedure was based on the acetylation of hydroxycoumarins; Fries rearrangement and Claisen–Schmidt condensation; the target 6-[5-aryl-4,5-dihydropyrazol-3-yl]-5-hydroxy-7-methylcoumarins (33–49) were obtained under reactions of hydrazine and 2-aryl-5-methyl-2,3-dihydropyrano[2,3-f]chromen-4,8-diones as the last phase of the protocol. Anticancer activity screening in NCI60-cell lines assay allowed identification of compound 47 with the highest level of antimitotic activity with mean GI50 value of 10.20 μM and certain sensitivity profile toward the Leukemia cell lines CCRF-CEM and MOLT-4 (GI50/TGI values 1.88/5.06 μM and 1.92/4.04 μM respectively).

Keywords

• Coumarins
• Pyronoflavanones
• Pyrazolines
• Anticancer activity