Synthesis and biological screening of a new series of 5-4-(4-aryl-1-piperazinyl)butoxycoumarins

摘要

A series of 5-4-(4-aryl-1-piperazinyl)butoxycoumarins were synthesized using microwave-assisted methods. The synthesized compounds were screened for their antibacterial activities against Gram-positive bacterial strains (Staphylococcus aureus, Micrococcus luteus, Bacillus cereus, Bacillus subtilis, Staphylococcus epidermidis, and Enterococcus hirae), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and for their antifungal activities against three species of Candida (Candida albicans and Candida parapsilosis). The 4,7-dimethyl-5-4-(pyridin-4-yl)butoxycoumarin and the 6-acetyl-4,7-dimethyl-5-4-(pyridin-4-yl)butoxycoumarin were the most active against the Gram-positive bacteria. The best minimum inhibitory concentration values were obtained for the 4,7-dimethyl-5-4-4-1-(4-pyridyl)piperazin-1-yl-butoxycoumarin against Micrococcus luteus (15 A mu g/cm(3)). Two tested compounds exhibited moderate to good antifungal activity. The antitumor activity against of the newly synthesized compounds was evaluated. Among all the compounds tested, the 6-acetyl-4,7-dimethyl-5-4-4-(2-fluorophenyl)piperazin-1-ylbutoxycoumarin was the most potent against HeLa cancer cells. Crystals of 4,7-dimethyl-5-4-4-(2-fluorophenyl)piperazin-1-ylbutoxycoumarin were investigated using a single crystal X-ray diffraction technique.