Environmentally friendly catalyst- and solvent-free synthesis of 2-anilino nicotinic acids derivatives as potential lead COX inhibitors

  • BMC Chem. 2023 Nov 20;17(1):160. doi: 10.1186/s13065-023-01078-y.
Mahsa Yarhorhosseini  1 ,  Shahrzad Javanshir  2 ,  Ahmad Shahir Sadr  3 ,  Milad Noori  1 ,  Navid Dastyafteh  1 ,  Maryam Esmkhani  1 ,  Aida Iraji  4  5 ,  Mohammad Mahdavi  6
Affiliations
  • 1. Heterocyclic Chemistry Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran.
  • 2. Heterocyclic Chemistry Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran. [email protected].
  • 3. Bioinformatics Research Center, Cheragh Medical Institute & Hospital, Kabul, Afghanistan. [email protected].
  • 4. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran. [email protected].
  • 5. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran. [email protected].
  • 6. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran.
PMID: 37986120 DOI: 10.1186/s13065-023-01078-y
Abstract

In this study, an environmentally friendly, solvent- and catalyst-free synthesis of 2-anilino nicotinic acids derivatives is reported. This operationally simple and green procedure was applied to a selection of primary aromatic amines giving rise to 23 derivatives of 2-anilino nicotinic acids in a very short reaction time (15-120 min) with good to excellent yield. Next, similarity searches were executed on these derivatives to find the possible biological target. These products were screened for inhibition of COX-1 and COX-2 by molecular docking and dynamic studies. In silico studies revealed that among these derivatives, the structure 10 bearing meta-chlorine substitutions could act as COX-1 and COX-2 inhibitors. These results can be used in designing important lead compounds for further development as potential anti-inflammatory drugs.

Keywords
2-Anilino nicotinic acids; COX; Molecular dynamic simulations; Similarity search; Solvent -free synthesis.
Products