Synthesis and molecular docking studies of xanthone attached amino acids as potential antimicrobial and anti-inflammatory agents

Abstract

A series of novel xanthone conjugated amino acids were synthesised and characterised by analytical and spectroscopic methods. All the synthesized analogues () were screened for their antimicrobial and anti-inflammatory activities. Compounds, ,, ,, ,, and showed excellent antimicrobial activities compared to antibacterial and antifungal reference drugs gentamicin and bavistin, respectively. Compounds and 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 , and showed the highest docking scores for antimicrobial activity while compounds, and showed the highest docking scores for anti-inflammatory activity. Different amino acids conjugated xanthone derivatives were synthesized and evaluated for their biological activities. The conjugation was found to play a major role in improving the biological activities of those compounds.

Chiral Derivatives of Xanthones with Antimicrobial Activity

“…Inspired by natural xanthone properties, and by Dahiya and collaborators [95] work of iodoquinazolinones and nitroimidazoles conjugated with amino acids which presented strong antimicrobial activity, led Chen et al [96] to synthesize xanthone derivatives with conjugated l -amino acids (Table 9).…”

“…The antimicrobial effect comes from the penetration of the amino acid hydrophobic chains in the bacterial membranes where the cationic moiety of the amino acids interacts with the membrane phospholipids disturbing the bacterial membrane. This is a strategy to develop new antimicrobial agents [96]. Due to the membrane’s essential properties, its disruption would lead to death without mutations resulting in loss of recognition by the antibiotics, leading to ineffective treatments [5].…”

Study on Synthesis and Biological Evaluation of 3-Aryl Substituted Xanthone Derivatives as Novel and Potent Tyrosinase Inhibitors

“…Xanthones are a class of oxygen-containing heterocycles with γ-pyran moiety condensed with two benzene rings, which are widely distributed in nature. 18) In recent years, xanthone derivatives have been received considerable attention in the field of medicinal chemistry because of their diversely biological functions, 20,21) such as anti-oxidant, 22) anti-hypertensive, 23) anti-convulsant, 24) anti-cholinesterase, 25) anti-malarial, 26) antimicrobial, 27) anti-inflammatory, 28) and anti-cancer activities. 29) Besides, they also served as the effective inhibitors of several enzymes like α-glycosidase, 30,31) topoisomerase, 32) proteinkinase, 33) aromatase.…”

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

“…Inspired by natural xanthones properties, Rakesh et al [ 184 ] synthesize xanthone derivatives with conjugated L-amino acids ( 244 – 263 , Figure 21 ), to determine the corresponding antimicrobial and anti-inflammatory activities. The same research group recently reported the evaluation of in vitro anticancer activity of those compounds, against three different cancer cell lines, MCF-7, MDA-MB-435 and A549, validated by DNA binding and molecular docking approaches [ 185 ].…”