Abstract
•A series of sulfonated esters of piroxicam 1–19 were synthesized.•The structures were confirmed by 1H-NMR, MS, IR, UV and elemental analysis.•All derivatives of piroxicam showed varying degree of antiglycation potential with IC50 values in range of 178.9 - 636.41 µM.•The structure-activity relationship was established.
A series of sulfonated esters of piroxicam 1–19 were synthesized by substitution of “H” from hydroxyl “OH” group of piroxicam with different alkyl/aryl sulfonyl chloride by continuous stirring at room temperature. The derivatives were elucidated through various spectroscopic procedures like 1H NMR, MS, IR, UV and elemental analysis. Piroxicam derivatives were screened for antiglycation activity, in order to analyze the effect of substitution for the management of late diabetic complications. The preliminary results showed that the compounds 2 exhibited potent antiglycation activity far better than the reference (rutin IC50 = 274.5 ± 0.05 µM), while the compounds 5 and 8 were near with IC50 values of 178.9 ± 1.55 µM, 237 ± 2.01 µM, and 256.5 ± 2.56 µM respectively. Moreover a negative effect of electron withdrawing groups was observed over the inhibition potential of different analogues depending upon the number and the positions of the substituents.
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