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Article

Green Synthesis, Characterization, and Biological Activity of 4-Aminoquinoline Derivatives: Exploring Antibacterial Efficacy, MRSA Inhibition, and PBP2a Docking Insights

by
Lo’ay A. Al-Momani
1,*,
Ula A. Abu Shawar
1,
Ayman H. Abu Sarhan
1,
Rand Shahin
2,
Panayiotis A. Koutentis
3,
Mohammad K. Abu-Sini
4 and
Nada J. Mohammad
4
1
Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
2
Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
3
Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus
4
Department of Pharmacy, Faculty of Pharmacy, Al-Zaytoonah University of Jordan, P.O. Box 130, Amman 11733, Jordan
*
Author to whom correspondence should be addressed.
Chemistry 2025, 7(3), 71; https://doi.org/10.3390/chemistry7030071
Submission received: 6 February 2025 / Revised: 8 April 2025 / Accepted: 15 April 2025 / Published: 25 April 2025
(This article belongs to the Section Molecular Organics)
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Abstract

A series of 4-aminoquinoline derivatives were prepared using a microwave-assisted method. The reactions were initially carried out on a small scale and subsequently scaled up using a sealed tube. Heating the reactions to 90–150 °C for 90–120 minutes obtained products with up to 95% yields. Structural analysis and characterization were achieved using FT-IR, 1H- and 13C-NMR spectroscopy and HR-MS. Four compounds displayed low-to-moderate antibacterial activity, with 6-chlorocyclopentaquinolinamine (7b) exhibiting potent inhibition against MRSA (MIC = 0.125 mM) and 2-fluorocycloheptaquinolinamine (9d) showing activity against S. pyogenes (MIC = 0.25 mM). Structure–activity relationship (SAR) docking studies within the Penicillin Binding Protein (PBP2a) binding site (PDB: 4DK1) showed that compounds 7b and 5b (7-chlorophenylquinolinamine) bind through hydrophobic interactions (ALA601, ILE614), hydrogen bonding (GLN521), and halogen contacts (TYR519, THR399). Compound 7b demonstrated enhanced MRSA inhibition due to additional π-alkyl interactions and optimal docking parameters. Conversely, the bulky structure of 9d may explain its weaker activity as it likely hindered binding to the target site. This paper highlights the role of structural features in antibacterial efficacy and guides the future optimization of 4-aminoquinoline derivatives.
Keywords: green synthesis; microwave-assisted synthesis; 4-aminoquinoline derivatives green synthesis; microwave-assisted synthesis; 4-aminoquinoline derivatives
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MDPI and ACS Style

Al-Momani, L.A.; Shawar, U.A.A.; Sarhan, A.H.A.; Shahin, R.; Koutentis, P.A.; Abu-Sini, M.K.; Mohammad, N.J. Green Synthesis, Characterization, and Biological Activity of 4-Aminoquinoline Derivatives: Exploring Antibacterial Efficacy, MRSA Inhibition, and PBP2a Docking Insights. Chemistry 2025, 7, 71. https://doi.org/10.3390/chemistry7030071

AMA Style

Al-Momani LA, Shawar UAA, Sarhan AHA, Shahin R, Koutentis PA, Abu-Sini MK, Mohammad NJ. Green Synthesis, Characterization, and Biological Activity of 4-Aminoquinoline Derivatives: Exploring Antibacterial Efficacy, MRSA Inhibition, and PBP2a Docking Insights. Chemistry. 2025; 7(3):71. https://doi.org/10.3390/chemistry7030071

Chicago/Turabian Style

Al-Momani, Lo’ay A., Ula A. Abu Shawar, Ayman H. Abu Sarhan, Rand Shahin, Panayiotis A. Koutentis, Mohammad K. Abu-Sini, and Nada J. Mohammad. 2025. "Green Synthesis, Characterization, and Biological Activity of 4-Aminoquinoline Derivatives: Exploring Antibacterial Efficacy, MRSA Inhibition, and PBP2a Docking Insights" Chemistry 7, no. 3: 71. https://doi.org/10.3390/chemistry7030071

APA Style

Al-Momani, L. A., Shawar, U. A. A., Sarhan, A. H. A., Shahin, R., Koutentis, P. A., Abu-Sini, M. K., & Mohammad, N. J. (2025). Green Synthesis, Characterization, and Biological Activity of 4-Aminoquinoline Derivatives: Exploring Antibacterial Efficacy, MRSA Inhibition, and PBP2a Docking Insights. Chemistry, 7(3), 71. https://doi.org/10.3390/chemistry7030071

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