Synthesis, antibacterial and antifungal activity of new 3-biphenyl-3H-Imidazo[1,2-a]azepin-1-ium bromides

Sergii Demchenko; Roman Lesyk; Johannes Zuegg; Alysha G Elliott; Yuliia Fedchenkova; Zinaida Suvorova; Anatolii Demchenko

doi:10.1016/j.ejmech.2020.112477

Synthesis, antibacterial and antifungal activity of new 3-biphenyl-3H-Imidazo[1,2-a]azepin-1-ium bromides

Eur J Med Chem. 2020 Sep 1:201:112477. doi: 10.1016/j.ejmech.2020.112477. Epub 2020 Jun 6.

Authors

Sergii Demchenko¹, Roman Lesyk², Johannes Zuegg³, Alysha G Elliott³, Yuliia Fedchenkova⁴, Zinaida Suvorova¹, Anatolii Demchenko⁵

Affiliations

¹ Institute of Pharmacology and Toxicology, Antona Tsedika 14, 03057, Kyiv, Ukraine.
² Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010, Lviv-10, Ukraine; Department of Public Health, Dietetics and Lifestyle Disorders, Faculty of Medicine, University of Information Technology and Management in Rzeszow, Sucharskiego 2, 35-225, Rzeszow, Poland. Electronic address: dr_r_lesyk@org.lviv.net.
³ The Community for Open Antimicrobial Drug Discovery (CO-ADD), Centre for Superbug Solutions, Institute for Molecular Bioscience, The University of Queensland, Brisbane, 4072, Australia.
⁴ Nizhyn Mykola Gogol State University, Grafska 2, Nizhyn, Ukraine.
⁵ Institute of Pharmacology and Toxicology, Antona Tsedika 14, 03057, Kyiv, Ukraine; Nizhyn Mykola Gogol State University, Grafska 2, Nizhyn, Ukraine.

PMID: 32619924
DOI: 10.1016/j.ejmech.2020.112477

Abstract

Novel 1-aryl-3-biphenyl-4-yl-3-hydroxy-2,5,6,7,8,9-hexahydro-3H-imidazo[1,2-a]azepin-1-ium bromides and their 2,5-dehydrogenated analogues were designed and synthesized using a reaction of aryl-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-amines with 1-biphenyl-4-yl-2-bromoethanone. Among the 16 novel compounds 5 derivatives displayed in vitro antimicrobial activity; while three of them showed promising activity against Staphylococcus aureus, Cryptococcus neoformans and Candida albicans.

Keywords: 3-Biphenyl-3H-imidazo[1,2-a]azepin-1-ium bromides; Antibacterial activity; Antifungal activity; In vitro tests; Minimum inhibitory concentration.

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / pharmacology*
Anti-Bacterial Agents / toxicity
Antifungal Agents / chemical synthesis
Antifungal Agents / pharmacology*
Antifungal Agents / toxicity
Azepines / chemical synthesis
Azepines / pharmacology*
Azepines / toxicity
Bacteria / drug effects
Fungi / drug effects
HEK293 Cells
Hemolysis / drug effects
Humans
Imidazoles / chemical synthesis
Imidazoles / pharmacology*
Imidazoles / toxicity
Microbial Sensitivity Tests
Molecular Structure
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Antifungal Agents
Azepines
Imidazoles