Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds
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Anas J. Rasras
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Mohamed El-Naggar
Abstract
A new series of aminoacetylenic nitroimidazole piperazine hybrid compounds were prepared via three-component reaction. Mannich-type reaction was utilized to couple the nitroimidazole containing propargylic moiety with secondary amines and formaldehyde in the presence of Cu (I) catalyst. The newly synthesized molecules 10a–10w, were characterized an ambiguously through NMR and mass spectrometry. The prepared compounds were assessed in vitro for their antibacterial activity against selected gram-positive and gram-negative bacteria. All of the compounds had shown insignificant activities toward gram-negative bacteria. While compounds 10m, 10q, 10s and 10t had shown moderate activities against the gram–positive bacteria Staphylococcus aureus, Bacillus subtilis and against fungi Escherichia coli and Proteus vulgaris.
Acknowledgements
This work has been carried out during sabbatical leave granted to the author (Raed A. Al-Qawasmeh) from the University of Jordan during the academic year 2020–2021.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: Authors wish to thank the Scientific Research Support Fund/Ministry of Higher Education, Jordan (grant No. Bas 1/1/2017) and RISE-University of Sharjah for technical support.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2022-0043).
© 2022 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Editorial
- Organic chemistry and medicinal applications
- Research Articles
- Nitroimidazoles Part 10. Synthesis, crystal structure, molecular docking, and anticancer evaluation of 4-nitroimidazole derivatives combined with piperazine moiety
- Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents
- Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds
- Design, synthesis, and molecular docking study of novel cinnoline derivatives as potential inhibitors of tubulin polymerization
- Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon
- Thermodynamic control synthesis of spiro[oxindole-3,3′-pyrrolines] via 1,4-dipolar cycloaddition utilizing imidazo[1,5-a]quinoline
- Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity
- 8-Amino-7-(aryl/hetaryl)fluoroquinolones. An emerging set of synthetic antibacterial agents
Artikel in diesem Heft
- Frontmatter
- Editorial
- Organic chemistry and medicinal applications
- Research Articles
- Nitroimidazoles Part 10. Synthesis, crystal structure, molecular docking, and anticancer evaluation of 4-nitroimidazole derivatives combined with piperazine moiety
- Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents
- Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds
- Design, synthesis, and molecular docking study of novel cinnoline derivatives as potential inhibitors of tubulin polymerization
- Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon
- Thermodynamic control synthesis of spiro[oxindole-3,3′-pyrrolines] via 1,4-dipolar cycloaddition utilizing imidazo[1,5-a]quinoline
- Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity
- 8-Amino-7-(aryl/hetaryl)fluoroquinolones. An emerging set of synthetic antibacterial agents
