Design, Synthesis and Bioevaluation of Highly Functionalized 1,2,3-Triazole-Guanidine Conjugates as Anti-Inflammatory and Antioxidant Agents

In search of new biologically potent molecules a small focused library of new guanidine-1,2,3-triazole hybrid derivatives were synthesized via Organocatalytic enolate- mediated azide-carbonyl [3 + 2] cycloaddition yielding a highly functionalized triazole core structure. The synthesis of all the der...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2023-07, Vol.43 (6), p.5567-5581
Main Authors: Siddiqui, Madiha A., Nagargoje, Amol A., Shaikh, Mubarak H., Siddiqui, Rashiqua A., Pund, Amit A., Khedkar, Vijay M., Asrondkar, Ashish, Deshpande, Prathmesh P., Shingate, Bapurao B.
Format: Article
Language:English
Subjects:
1,2,3-Triazole
anti-inflammatory
Anti-inflammatory agents
Antioxidant
Antioxidants
Binding
Carbonyl compounds
Carbonyls
Conjugates
COX-2 Inhibitor
Cycloaddition
Diclofenac
Enzymes
Guanidine
Inflammation
Molecular docking
molecular hybridization
NMR
Nuclear magnetic resonance
Pharmacology
Prostaglandin endoperoxide synthase
Spectral analysis
Spectrum analysis
Synthesis
Triazoles
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Summary:In search of new biologically potent molecules a small focused library of new guanidine-1,2,3-triazole hybrid derivatives were synthesized via Organocatalytic enolate- mediated azide-carbonyl [3 + 2] cycloaddition yielding a highly functionalized triazole core structure. The synthesis of all the derivatives were confirmed by spectral analysis 1 H NMR, 13 C NMR and MS. The new guanidine-1,2,3-triazole conjugates were found to exhibit promising anti-inflammatory and antioxidant activity. The anti-inflammatory activity screened by membrane stabilization method summarizes the four potential conjugates 5c, 5f, 5h and 5g to be potent in comparison with standard drug Diclofenac sodium (DFS). The conjugates were also assessed for antioxidant potential by DPPH method. Among all the synthesized compounds, the compounds 5d, 5f, 5g and 5h exhibited potent antioxidant activity. Molecular docking study was performed to gain insight into the putative binding mode and binding strength of these compounds with the target enzyme Cyclo-oxygenase (COX-2) enzyme. The in vitro and in silico studies together with simpler designing and synthesis strategy via Organocatalytic enolate- mediated azide-carbonyl [3 + 2] cycloaddition followed by a two-component reaction with guanidine in basic conditions rationalize guanidine-1,2,3-triazole hybrid derivatives as easily assessable novel therapeutic agents.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2022.2105904