Synthesis, in vitro anti-urease, in-silico molecular docking study and ADMET predictions of piperidine and piperazine Morita-Baylis-Hillman Adducts (MBHAs)
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Samina Aslam
,
Hamid Ullah
Abstract
The current work describes an efficient synthesis of Morita-Baylis-Hillman adducts (MBHAs) derived heterocycles (4, 5, 6, 7, 10, 11, 12, 13, 16 and 17) with the Michael addition of piperidine and piperazine heterocycles. The comparative studies of mono and di-hydrogen bond acceptors heterocycles, meta and para substituted nitro-phenyl rings and the isolated single diastereomer 16 through molecular docking coupled with in vivo bioactivities displayed very important results. The biological significances were observed against urease enzyme (IC50 = 3.95 ± 0.10 µM). Almost all the compounds displayed different ranges of inhibition potential whereas the di-hydrogen bond donor diastereomers 12 and 13 were found to be highly potent against the targeted enzyme while the remaining had shown comparable inhibitory activity. The diastereomers 12 and 13 were the most active having minimum inhibitory concentration (MIC) IC50 = 3.95 ± 0.10 µM. All the synthesized compounds were docked and their best poses were explored for enhanced biological properties. The molecular docking studies revealed better binding interactions of the ligand with the target enzyme. Furthermore, ADMET predictions were also observed which revealed drug like properties for all the novel MBHAs based piperidine and piperazine derivatives.
Acknowledgments
The authors would like to extend their sincere appreciation to Researchers Support from the Higher Education Commission, Pakistan and the University of Balochistan, Quetta.
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Research ethics: Not applicable.
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Informed consent: Not applicable.
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Author contributions: Conceptualization, S.U. and H.U.; methodology, S.A.; software, Y.K. and N.K.; validation, A.R. and S.A.; formal analysis, S.U.; investigation, H.U. and A.B.; data curation, S.A. and A.B.; writing – original draft preparation, S.A., and S.U.; writing – review and editing, S.U., and A.R., A.B.; project administration, S.U. All authors have read and agreed to the published version of the manuscript.
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Use of Large Language Models, AI and Machine Learning Tools: None declared.
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Conflict of interest: The author states no conflict of interest.
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Research funding: None declared.
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Data availability: Not applicable.
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Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/znc-2024-0175).
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Articles in the same Issue
- Frontmatter
- Review Articles
- Ethnopharmacology and current conservational status of Cordyceps sinensis
- Review perspective on advanced nutrachemicals and anterior cruciate ligament rehabilitation
- Research Articles
- Cytotoxic compounds from Viscum coloratum (Kom.) Nakai
- Effect of Hibiscus sabdariffa L. leaf flavonoid-rich extract on Nrf-2 and HO-1 pathways in liver damage of streptozotocin-induced diabetic rats
- Inhibition of pro-inflammatory cytokines by homalolide A and homalomenol A isolated from rhizomes of Homalomena pendula
- Synthesis, in vitro anti-urease, in-silico molecular docking study and ADMET predictions of piperidine and piperazine Morita-Baylis-Hillman Adducts (MBHAs)
- Molecular modeling and synthesis of novel benzimidazole-derived thiazolidinone bearing chalcone derivatives: a promising approach to develop potential anti-diabetic agents
- Determination of essential oil and phenolic compounds of Berberis vulgaris grown in Şavşat, Artvin; revealing its antioxidant and antimicrobial activities
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