ArticleCurrent medicinal chemistry2025
Mechanochemical Synthesis of Diclofenac Conjugates with Glucosamine and Chitosan Exhibiting COX-2 Selective Ulcer Safe Anti-inflammatory Activity.
Article in Current medicinal chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
introductionNon-steroidal anti-inflammatory drugs are associated with severe gastrointestinal irritation upon prolonged use, largely due to their carboxylic (-COOH) functional group.
aimTo address this issue, we aimed to synthesize diclofenac conjugates with glucosamine and chitosan, converting the -COOH group into an amide (-CONH-) via a mechanochemical, environmentally friendly method.
methodsIn this study, diclofenac acid was first converted to its acid chloride using thionyl chloride under mechanochemical conditions and subsequently reacted with glucosamine base and chitosan. The resulting conjugates were evaluated for anti-inflammatory activity through the rat-paw edema test, along with ulcerogenicity, COX inhibition assays, and cardiovascular assessment.
resultsThe mechanochemical approach provided high yields (>90%) and resulted in conjugates that significantly reduced paw edema (62.3 ± 2.3% for diclofenacglucosamine and 58.5 ± 1.6% for diclofenac-chitosan) compared to diclofenac sodium (49.0 ± 1.3%) after 5 h. Notably, the conjugates were ulcer safe, as no gastric lesions were observed, unlike the multiple lesions detected in animals treated with diclofenac sodium. Both conjugates also demonstrated a high degree of COX-2 selectivity and cardiovascular safety.
conclusionThis study highlights the potential of mechanochemical synthesis for efficient amide formation, avoiding the need for hydroxyl group protection.
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