Synthesis and biological activity of novel 4-nicotinoyl-1,7-di(pyridi- ne-3-yl)-3,5-diaryl heptane-1,7-dione under Claisen-Schmidt condensation

Geetha, D. and Basavaraju, B. Y. and Roopa, K. (2025) Synthesis and biological activity of novel 4-nicotinoyl-1,7-di(pyridi- ne-3-yl)-3,5-diaryl heptane-1,7-dione under Claisen-Schmidt condensation. Journal of Molecular Structure, 1344 (142979). ISSN 00222860

Text a5.pdf Download (9MB)

Abstract

The focus of the research is on the unexpected products that resulted from the condensation reaction between 3- acetyl pyridine (1) and various heterocyclic aldehydes 2(a-h) under the conditions of the Claisen-Schmidt re- action. Chalcone derivatives were produced in good yield 3(a-h) by various heterocyclic aldehydes in the presence of aqueous alkaline bases. The latest synthesis of chalcones with N, O, S heterocycles has shown their potential biological value in the post-decade period. The chalcone compounds formed, which are immediately converted into unexpected 4-nic- otinoyl-1,7-di(pyridine-3-yl)-3,5-diaryl heptane-1,7‑dione in the same reaction. The melting point, elemental analysis, MS, FTIR, 1H NMR, and 13C NMR spectroscopic data were used to confirm the structure of produced compounds. A large number of heterocyclic chalcones have better activity than the standard ones. The antibacterial activity of the produced compounds against various bacterial and fungal species was also assessed in vitro. Studies on docking and anticancer were also conducted. Of the compounds that were syn- thesised, 3g and 3h showed the highest potency due to the presence of a halogen atom. The synthesised compounds were assessed for their in vitro antibacterial and antifungal potential towards several pathogenic bacterial and fungal strains by the agar well diffusion method. All these compounds showed moderate to good antimicrobial activity. The most active antimicrobial compounds, 3g and 3h, were further evaluated for their antioxidant potency by 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis(3-ethyl- benzothiazolin-6-sulfonic acid) (ABTS.+) cation radical decolorisation assays. Anti-inflammatory efficacy of these compounds was tested by lipoxygenase (LOX) inhibition assay. These derivatives were also assessed for their cytotoxicity towards human lung cancer cells by MTT assay. The compounds 3g and 3h have shown good antioxidative, anti-inflammatory, and anti-cancer activity. The molecular docking analysis was performed using the compound 3d with S. aureus enterotoxin, P. aeruginosa bacterioferritin B, anticancer protein human BCL-2 isoform, and lipoxygenase to ascertain the probable binding model

Item Type:	Article
Uncontrolled Keywords:	Aldehydes; Antioxidants; Bacteria; Bioactivity; Condensation reactions; Diseases; Fungi; Halogen compounds; Heptane; Pyridine; Spectroscopic analysis; Synthesis (chemical)
Divisions:	Department of > Chemistry
Depositing User:	Vasantha library uom
Date Deposited:	28 Nov 2025 06:04
Last Modified:	28 Nov 2025 06:04
URI:	http://eprints.uni-mysore.ac.in/id/eprint/18075

Actions (login required)

View Item