Synthesis and biological evaluation of novel 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines as potential anti-bacterial agents

Egor V Verbitskiy; Svetlana A Baskakova; Natal'ya A Gerasimova; Natal'ya P Evstigneeva; Natal'ya V Zil'berberg; Nikolay V Kungurov; Marionella A Kravchenko; Sergey N Skornyakov; Marina G Pervova; Gennady L Rusinov; Oleg N Chupakhin; Valery N Charushin

doi:10.1016/j.bmcl.2017.05.013

Synthesis and biological evaluation of novel 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines as potential anti-bacterial agents

Bioorg Med Chem Lett. 2017 Jul 1;27(13):3003-3006. doi: 10.1016/j.bmcl.2017.05.013. Epub 2017 May 6.

Affiliations

¹ Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str, 22, Ekaterinburg 620990, Russia; Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia. Electronic address: Verbitsky@ios.uran.ru.
² Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str, 22, Ekaterinburg 620990, Russia.
³ Ural Research Institute for Dermatology, Venereology and Immunopathology, Scherbakova St., 8, Ekaterinburg 620076, Russia.
⁴ Ural Research Institute for Phthisiopulmonology, 22 Parts'ezda St, 50, Ekaterinburg 620039, Russia.
⁵ Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str, 22, Ekaterinburg 620990, Russia; Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia.

PMID: 28512023
DOI: 10.1016/j.bmcl.2017.05.013

Abstract

A facile two-step synthetic approach to fluorinated and non-fluorinated 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines from readily available 5-bromo-4-(furan-2-yl)pyrimidine has been developed. All synthesized compounds were screened in vitro for their antibacterial activities against twelve various bacterial strains. It is demonstrated that some of these compounds exhibited significant antibacterial activities against strains Neisseria gonorrhoeae and Staphylococcus aureus, comparable and even higher with that commercial drug Spectinomycin.

Keywords: Antigonorrheal; Antimycobacterial; Nitrofuran; Nucleophilic aromatic substitution of hydrogen; Pyrimidine.

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Dose-Response Relationship, Drug
Microbial Sensitivity Tests
Molecular Structure
Neisseria gonorrhoeae / drug effects*
Nitro Compounds / chemical synthesis
Nitro Compounds / chemistry
Nitro Compounds / pharmacology*
Pyrimidines / chemical synthesis
Pyrimidines / chemistry
Pyrimidines / pharmacology*
Staphylococcus aureus / drug effects*
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Nitro Compounds
Pyrimidines