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Vol. 36 No. 3 (2024): Vol 36 Issue 3, 2024

Copyright (c) 2024 Ramesh Domala, KADEER MD

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Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine

https://doi.org/10.14233/ajchem.2024.30953
Kadeer Md
1Department of Chemistry, Mahatma Gandhi University, Nalgonda-508254, India 2Chemistry Division, CVR College of Engineering, Hyderabad-501510, India
https://orcid.org/0009-0000-8011-7775
Ramesh Domala
Department of Chemistry, Mahatma Gandhi University, Nalgonda-508254, India
https://orcid.org/0000-0002-8197-4709

Corresponding Author(s) : Ramesh Domala

drdo.ramesh3@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 3 (2024): Vol 36 Issue 3, 2024

Abstract

Present study establishes a novel synthetic route of N-acetylated derivatives of 5-(2-phenyl-1,8-naphthyridine-3-yl)-1,3,4-oxadiazole-2-amine (6a-j), which was achieved in four steps with good yields. 2-Amino nicotinaldehyde and ethyl 3-oxo-3-phenylpropanoate on refluxing with triethylamine in ethanol undergoes Friedlander synthesis to furnish ethyl 2-phenyl-1,8-naphthyridine-3-carboxylate, which further converted into 2-phenyl-1,8-naphthyridine-3-carbohydrazide by reacting with hydrazine hydrate upon reflux, followed by cyclization with cyanogen bromide in the presence of water and 1,4-dioxane with sodium bicarbonate to afford 5-(2-phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine (5). Compound 5 was acetylated using numerous symmetrical anhydrides to synthesize novel N-acetylated derivatives (6a-j). The IR, 1H, 13C NMR and mass spectral analysis were used to characterize the structure of synthetic compounds. The synthesized compounds were evaluated for their antimicrobial efficiency against bacteria (S. aureus and E. coli) using ampicillin as a standard reference and against fungi (C. albicans) using fluconazole as a standard reference. Compound 6e exhibited good antibacterial properties while compounds 6c and 6e had shown high antifungal activity, whereas remaining compounds shown moderate to weaker antimicrobial activity. The synthesized derivatives verified their docking strength against Mtb MurB (PDB ID: 5JZX) and showed significant docking activity, however, compound 6f (-10.98 kcal/mol) and compound 6b (-10.52 kcal/mol) had a strong binding affinity compared to the other synthesized compounds.

Keywords

1,8-Naphthyridine Oxadiazole Antimicrobial properties Docking study
Md, K., & Domala, R. (2024). Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine. Asian Journal of Chemistry, 36(3), 628–634. https://doi.org/10.14233/ajchem.2024.30953
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