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Article

Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies

by
Ghofrane Lahmadi
1,2,
Mabrouk Horchani
2,
Amal Dbeibia
3,
Abdelkarim Mahdhi
3,
Anis Romdhane
2,
Ata Martin Lawson
1,
Adam Daïch
1,
Abdel Halim Harrath
4,
Hichem Ben Jannet
2,* and
Mohamed Othman
1,*
1
Normandie University, URCOM, UNILEHAVRE, FR3021, UR 3221, 25 Rue Philippe Lebon, BP 540, F-76058 Le Havre, France
2
Laboratory of Heterocyclic Chemistry, LR11ES39, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, Monastir 5019, Tunisia
3
Laboratory of Analysis, Treatment and Valorization of Pollutants of the Environment and Products, Faculty of Pharmacy, University of Monastir, Monastir 5000, Tunisia
4
Department of Zoology, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Molecules 2023, 28(12), 4655; https://doi.org/10.3390/molecules28124655
Submission received: 18 May 2023 / Revised: 4 June 2023 / Accepted: 6 June 2023 / Published: 8 June 2023
(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)
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Abstract

As part of the valorization of agricultural waste into bioactive compounds, a series of structurally novel oleanolic acid ((3β-hydroxyolean-12-en-28-oic acid, OA-1)-phtalimidines (isoindolinones) conjugates 18a–u bearing 1,2,3-triazole moieties were designed and synthesized by treating an azide 4 previously prepared from OA-1 isolated from olive pomace (Olea europaea L.) with a wide range of propargylated phtalimidines using the Cu(I)-catalyzed click chemistry approach. OA-1 and its newly prepared analogues, 18a–u, were screened in vitro for their antibacterial activity against two Gram-positive bacteria, Staphylococcus aureus and Listeria monocytogenes, and two Gram-negative bacteria, Salmonella thyphimurium and Pseudomonas aeruginosa. Attractive results were obtained, notably against L. monocytogenes. Compounds 18d, 18g, and 18h exhibited the highest antibacterial activity when compared with OA-1 and other compounds in the series against tested pathogenic bacterial strains. A molecular docking study was performed to explore the binding mode of the most active derivatives into the active site of the ABC substrate-binding protein Lmo0181 from L. monocytogenes. Results showed the importance of both hydrogen bonding and hydrophobic interactions with the target protein and are in favor of the experimental data.
Keywords: oleanolic acid; phtalimidines; triazole; click chemistry; antibacterial activity; molecular docking oleanolic acid; phtalimidines; triazole; click chemistry; antibacterial activity; molecular docking

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MDPI and ACS Style

Lahmadi, G.; Horchani, M.; Dbeibia, A.; Mahdhi, A.; Romdhane, A.; Lawson, A.M.; Daïch, A.; Harrath, A.H.; Ben Jannet, H.; Othman, M. Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies. Molecules 2023, 28, 4655. https://doi.org/10.3390/molecules28124655

AMA Style

Lahmadi G, Horchani M, Dbeibia A, Mahdhi A, Romdhane A, Lawson AM, Daïch A, Harrath AH, Ben Jannet H, Othman M. Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies. Molecules. 2023; 28(12):4655. https://doi.org/10.3390/molecules28124655

Chicago/Turabian Style

Lahmadi, Ghofrane, Mabrouk Horchani, Amal Dbeibia, Abdelkarim Mahdhi, Anis Romdhane, Ata Martin Lawson, Adam Daïch, Abdel Halim Harrath, Hichem Ben Jannet, and Mohamed Othman. 2023. "Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies" Molecules 28, no. 12: 4655. https://doi.org/10.3390/molecules28124655

APA Style

Lahmadi, G., Horchani, M., Dbeibia, A., Mahdhi, A., Romdhane, A., Lawson, A. M., Daïch, A., Harrath, A. H., Ben Jannet, H., & Othman, M. (2023). Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies. Molecules, 28(12), 4655. https://doi.org/10.3390/molecules28124655

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