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Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical
Mohammed-Yassin Hjouji1, Ahmed M Almehdi2, Hicham Elmsellem3
1Laboratory of Applied Organic Chemistry, Faculty of Science and Technology Saiss, Sidi Mohammed Ben Abdallah University, Fez 30050, Morocco.
Molecules (Basel, Switzerland)
|April 13, 2023
Summary
This study synthesized novel imidazo[4,5-b]pyridine derivatives and explored their antibacterial potential. Compounds 2 and 4 showed promising activity against Gram-positive bacteria, suggesting therapeutic applications.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Computational Chemistry
- Antimicrobial Research
Background:
- Imidazo[4,5-b]pyridine scaffolds are recognized for their diverse biological activities.
- Exploring novel derivatives is crucial for identifying new therapeutic agents.
- Understanding structure-activity relationships aids in drug design.
Purpose of the Study:
- To synthesize a series of novel 6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridine derivatives.
- To investigate the regioselectivity of alkylation reactions on the imidazo[4,5-b]pyridine core.
- To evaluate the synthesized compounds' potential as antibacterial agents.
Main Methods:
- Synthesis of 6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridine via condensation reaction.
- Regioselective alkylation using phase transfer catalysis (PTC) to yield N1, N3, and N4 isomers.
- Structural elucidation using NMR, X-ray diffraction, DFT calculations, and Hirshfeld analysis.
- Molecular docking studies against DHFR active sites.
- In vitro antibacterial activity testing against *Bacillus cereus* and *Escherichia coli*.
Main Results:
- Successful synthesis of target imidazo[4,5-b]pyridine derivatives (compounds 1-8).
- Alkylation reactions yielded mixtures of N1, N3, and N4 regioisomers.
- DFT calculations provided insights into electronic properties and reactivity.
- Molecular docking indicated favorable interactions with DHFR.
- Compounds 2 and 4 exhibited significant in vitro antibacterial activity, particularly against *Bacillus cereus*.
Conclusions:
- The study successfully synthesized and characterized novel imidazo[4,5-b]pyridine analogs.
- The synthesized compounds show potential as antibacterial agents, with greater efficacy against Gram-positive bacteria.
- Further development of these compounds could lead to new antimicrobial therapies.
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