Synthesis and biological evaluation of xanthen-1,8-dione derivatives

Abstract

Fourteen previously synthesized 3,3,6,6-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthen-1,8(2H)-dione derivatives were evaluated in vitro for their antimicrobial, antiproliferative and antioxidant activity. Also, in this work 3,3,6,6-tetramethyl-9-(4-acetamidophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthen-1,8(2H)-dione (15) was synthesized according to the same procedure and structure was confirmed by IR, NMR spectroscopy and mass spectrometry. Compounds were screened against Gram negative bacterium Pseudomonas aeruginosa and Gram positive bacteria Staphylococcus aureus and Bacillus subtilis. The antifungal activity of synthetized xanthene compounds was tested against fungus Saccharomyces cerevisiae. The cell lines HeLa, SW620, HEpG2, A549 and3T3 were targets for antiproliferative effects of synthesized compounds. The results showed that the most potent, as antimicrobial and antiproliferative agent, was compound with two atoms of bromine substituted on aryl ring, and the most potent antioxidant agent was compound 3,3,6,6-tetramethyl-9-(2-methoxy-3-hydroxy-4-nitrophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthen-1,8(2H)-dione with IC₅₀ of 0.045 mM and 70.41% of inhibition DPPH.