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Vol. 37 No. 12 (2025): Vol 37 Issue 12, 2025

Copyright (c) 2025 Ch. Soujanya, K. Madhavi

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Synthesis and Evaluation of Novel 5-{[2-Cyano-3-(substituted phenyl)prop-2-enoyl]amino}-2-hydroxy Benzoic Acid

https://doi.org/10.14233/ajchem.2025.34930
Ch. Soujanya
Department of Pharmaceutical Chemistry, Gokaraju Ranga Raju College of Pharmacy, Hyderabad-500090, India
https://orcid.org/0000-0002-5045-0515
K. Madhavi
Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati-571502, India
https://orcid.org/0000-0002-9564-8920

Corresponding Author(s) : Ch. Soujanya

soujanya8056@grcp.ac.in

Asian Journal of Chemistry, Vol. 37 No. 12 (2025): Vol 37 Issue 12, 2025

Abstract

5-Aminosalicylic acid (5-ASA), also known as mesalamine is extensively used for the treatment of inflammatory conditions like ulcerative colitis (UC), inflammatory bowel disease (IBD) and colorectal cancer. Hence, the current work aimed at the synthesis of some novel derivatives of 5-ASA involving cyanoacetylation and subsequent Knoevenagel condensation reaction. The compounds were then characterized using physical and spectral data and screened for in vitro antioxidant and anti-inflammatory activities. The compounds showed promising in vitro antioxidant and anti-inflammatory activities among which compound 4e (3,4-OCH3) exhibited superior dual antioxidant activity in DPPH and nitric oxide assays greater than ascorbic acid and 5-ASA. Meanwhile, compound 4l (-Cl) showed the strongest inhibition of protein denaturation and 4m (-F) exhibited highest protection of HRBC membrane. Further, PASS analysis identified 4j (4-CH(CH3)2), 4c (3,4-OH) and 4m (4-F) as promising anti-inflammatory candidates with favourable safety profiles when compared to 5-ASA. Overall, these derivatives showed good to moderate biological activity, suggesting for further evaluation under inflammatory conditions.

Keywords

5-Aminosalicylic acid Mesalamine Cyanoacetylation Knoevenagel condensation Antioxidant Anti-inflammatory
(1)
Soujanya, C.; Madhavi, K. Synthesis and Evaluation of Novel 5-{[2-Cyano-3-(substituted phenyl)prop-2-enoyl]amino}-2-Hydroxy Benzoic Acid. ajc 2025, 37, 3191-3198.
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