Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives

Abstract

Ten biologically active 2,2,5,5-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives were synthesized and their structures were confirmed by IR, 1 H and 13 C NMR spectroscopy and mass spectrometry. Synthesized compounds were scanned for their antioxidant, antimicrobial and antiproliferative activity. Antibacterial activity was tested by the diffusion and dilution method against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa, while antifungal activity was tested against Candida albicans and Saccharomyces cerevisiae. Antiproliferative activity was tested against HeLa (cervical carcinoma), SW620 (colorectal adenocarcinoma, metastatic), hepatocellular carcinoma (HEpG2), lung carcinoma cells (A549) and mouse embryo fibroblast cell line (3T3). The best antioxidant activity showed compound 2 with two hydroxy groups substituted on phenyl ring in positions 2' and 3'. The best antimicrobial activity of all synthesized compounds showed compound 8, while the best antiproliferative activity showed compound 6. Results signify the importance of xanthene-1,8-dione derivatives as potential antioxidant and antiproliferative agents.

Assisted ultrasonic wave of vanillin derivatives synthesis and antioxidant activity using DPPH method

“…al. [6], and the 1,8-dioxo-octahydroxantene derivative compound substituted with hydroxyl group revealed in the study by our previous publication [7,13]. The study carried out by Nirwani et al [26] presented that the hydroxyl group could hinder the free radicals reaction continuity through the hydrogen radical donation to the free radicals by hydroxyl group homolytic reaction producing more stable and less reactive free radicals.…”

“…Research carried out by Zukic et al [6] mentioned that the 1,8-dioxo-octahydroxantene derivatives substituted with hydroxyl groups in the ortho position and methoxy group in the meta position toward the benzene ring had an antioxidant activity with 62.83% inhibition and EC50 of 0.13 mM. Another study conducted by Retnosari et al [7] identified that 1,8dioxo-octahydroxantene derivatives substituted with hydroxyl groups in the para position toward the benzene ring had an antioxidant activity with lC50 of < 2 ppm.…”

Aloe Vera Extract-Mediated CuO NPs as Catalysts for the Synthesis of 4-Hydroxy-3-Methoxybenzaldehyde-Connected Piperidine Derivatives and Their Antibacterial Activity

“…Acetyl vanillin compounds have also been shown to have bactericidal action [2]. When OH group are present, antibacterial action against Pseudomonas strains is boosted [15]. Piperidine has been associated to antibacterial, antifungal, anticancer, anticonvulsant, and antihyperlipidemic activities [16][17][18][19][20][21][22][23].…”