In the present study, a series of fatty acids-based (short, medium and long unsaturated chains) glycosylated N-fatty acyl-L-tyrosines and N-lipoyl-L-tyrosine methyl esters were synthesized and evaluated for their cytotoxic and antimicrobial activities. The aglycone moiety was synthesized using different chemicalreagents. The glycosylation of aglycone moiety with different carbohydrates was performed using the Lewis acid, BF3.Et2O. All the synthesized compounds were tested against a panel of four cancer cell lines. The glycosylated N-fatty acyl-L-tyrosines showed moderate activity against all the cell lines and the IC50 values were in the range of 15.6−45.6 μM. However, the oleic acid analogues (10a, 10d) exhibited IC50 values of 15.6, 17.6 μM, respectively, against MDA-MB-231 cell line. Glycosylated N-lipoyl-L-tyrosine methyl esters (6b–6d) showed promising activity against all the tested cell lines and the IC50 values ranged between 9.4−13.8 μM. The compound 6d exhibited significant cytotoxicity and IC50 values were 10.5, 9.4, 10.9 and 12.1 μM against A549, PC3, MDA-MB-231 and HepG2 cell lines, respectively. Moreover, the nonglycosylated N-fatty acyl-L-tyrosine and methyl N-fatty acyl-L-tyrosinate derivatives showed excellent and moderate antimicrobial activity against some of the tested bacterial strains.
Volume 132, 2019
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