Synthesis and molecular docking studies of xanthone attached amino acids as potential antimicrobial and anti-inflammatory agentsElectronic supplementary information (ESI) available. See DOI: 10.1039/c7md00209b

A series of novel xanthone conjugated amino acids were synthesised and characterised by analytical and spectroscopic methods. All the synthesized analogues ( 2-23 ) were screened for their in vitro antimicrobial and anti-inflammatory activities. Compounds 7 , 8 , 9 , 12 , 18 , 19 , 20 , 21 and 23 showed excellent antimicrobial activities compared to antibacterial and antifungal reference drugs gentamicin and bavistin, respectively. Compounds 7-12 and 18-23 showed good anti-inflammatory activity compared to a standard drug, indomethacin. The preliminary structure-activity relationship revealed that tryptophan, tyrosine, phenylalanine, proline and cysteine conjugated compounds showed excellent antimicrobial and anti-inflammatory activities. This may be explained by the contribution of aromaticity and hydrophobicity of amino acids. Molecular docking studies were performed for all the synthesised compounds, among which compounds 20 , 21 and 23 showed the highest docking scores for antimicrobial activity while compounds 9 , 20 and 22 showed the highest docking scores for anti-inflammatory activity. Different amino acids conjugated xanthone derivatives were synthesized and evaluated for their in vitro biological activities. The conjugation was found to play a major role in improving the biological activities of those compounds. A series of novel xanthone conjugated amino acids were synthesised and characterised by analytical and spectroscopic methods.