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

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

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. shjavan@iust.ac.ir.
  • 3 Bioinformatics Research Center, Cheragh Medical Institute & Hospital, Kabul, Afghanistan. shahirsadr@gmail.com.
  • 4 Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran. aida.iraji@gmail.com.
  • 5 Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran. aida.iraji@gmail.com.
  • 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.

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