Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria
<b>Introduction/Objectives</b>: Nosocomial infections caused by <i>S. aureus</i> and <i>S. epidermidis</i> resistant strains are an important cause of morbidity and mortality worldwide. Due to the increasing rate of resistance to conventional antibiotics, the disc...
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-02-01
|
| Series: | Antibiotics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2079-6382/14/3/218 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850089788900638720 |
|---|---|
| author | Patrícia I. C. Godinho Paula Pérez-Ramos Yaiza Gabasa Enmanuel Cornielle Sara M. Soto Raquel G. Soengas Artur M. S. Silva |
| author_facet | Patrícia I. C. Godinho Paula Pérez-Ramos Yaiza Gabasa Enmanuel Cornielle Sara M. Soto Raquel G. Soengas Artur M. S. Silva |
| author_sort | Patrícia I. C. Godinho |
| collection | DOAJ |
| description | <b>Introduction/Objectives</b>: Nosocomial infections caused by <i>S. aureus</i> and <i>S. epidermidis</i> resistant strains are an important cause of morbidity and mortality worldwide. Due to the increasing rate of resistance to conventional antibiotics, the discovery of new antibiotic drugs is crucial to keep pace with the evolution of these pathogenic bacterial species. <b>Methods</b>: The 3-nitro-2<i>H</i>-chromene moiety is present in several compounds with potent antibacterial activity; based on these previous studies, we report herein the synthesis of 20 new 2-aryl-3-nitro-2<i>H</i>-chromene derivatives and the evaluation of their antibacterial potential in vitro. <b>Results</b>: Mono-halogenated nitrochromenes showed moderate anti-staphylococcal activity with MIC values of 8–32 μg/mL, whereas tri-halogenated 3-nitro-2<i>H</i>-chromenes displayed potent anti-staphylococcal activities with MIC values of 1–8 μg/mL. Notably, 2-(4-bromophenyl)-6-bromo-8-chloro-3-nitro-2<i>H</i>-chromene <b>5s</b> was the best antibacterial agent in the series against multidrug-resistant strains of <i>S. aureus</i> and <i>S. epidermidis</i> with MIC values of 4 μg/mL and 1–4 μg/mL, respectively. <b>Conclusions</b>: nitrochromene <b>5s</b> shows a good safety profile, so it can be considered as a lead for further development. |
| format | Article |
| id | doaj-art-a1f598e17c3e4e099ed5835677b3c7be |
| institution | DOAJ |
| issn | 2079-6382 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antibiotics |
| spelling | doaj-art-a1f598e17c3e4e099ed5835677b3c7be2025-08-20T02:42:41ZengMDPI AGAntibiotics2079-63822025-02-0114321810.3390/antibiotics14030218Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant BacteriaPatrícia I. C. Godinho0Paula Pérez-Ramos1Yaiza Gabasa2Enmanuel Cornielle3Sara M. Soto4Raquel G. Soengas5Artur M. S. Silva6LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalDepartment of Organic and Inorganic Chemistry, University of Oviedo, and Instituto Universitario de Química Organometálica Enrique Moles, C/Julián Clavería 8, 33006 Oviedo, SpainISGlobal, 08036 Barcelona, SpainISGlobal, 08036 Barcelona, SpainISGlobal, 08036 Barcelona, SpainDepartment of Organic and Inorganic Chemistry, University of Oviedo, and Instituto Universitario de Química Organometálica Enrique Moles, C/Julián Clavería 8, 33006 Oviedo, SpainLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal<b>Introduction/Objectives</b>: Nosocomial infections caused by <i>S. aureus</i> and <i>S. epidermidis</i> resistant strains are an important cause of morbidity and mortality worldwide. Due to the increasing rate of resistance to conventional antibiotics, the discovery of new antibiotic drugs is crucial to keep pace with the evolution of these pathogenic bacterial species. <b>Methods</b>: The 3-nitro-2<i>H</i>-chromene moiety is present in several compounds with potent antibacterial activity; based on these previous studies, we report herein the synthesis of 20 new 2-aryl-3-nitro-2<i>H</i>-chromene derivatives and the evaluation of their antibacterial potential in vitro. <b>Results</b>: Mono-halogenated nitrochromenes showed moderate anti-staphylococcal activity with MIC values of 8–32 μg/mL, whereas tri-halogenated 3-nitro-2<i>H</i>-chromenes displayed potent anti-staphylococcal activities with MIC values of 1–8 μg/mL. Notably, 2-(4-bromophenyl)-6-bromo-8-chloro-3-nitro-2<i>H</i>-chromene <b>5s</b> was the best antibacterial agent in the series against multidrug-resistant strains of <i>S. aureus</i> and <i>S. epidermidis</i> with MIC values of 4 μg/mL and 1–4 μg/mL, respectively. <b>Conclusions</b>: nitrochromene <b>5s</b> shows a good safety profile, so it can be considered as a lead for further development.https://www.mdpi.com/2079-6382/14/3/218chromenesnitro derivativesantibacterialMDR bacteriahalogenated drugs |
| spellingShingle | Patrícia I. C. Godinho Paula Pérez-Ramos Yaiza Gabasa Enmanuel Cornielle Sara M. Soto Raquel G. Soengas Artur M. S. Silva Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria Antibiotics chromenes nitro derivatives antibacterial MDR bacteria halogenated drugs |
| title | Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria |
| title_full | Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria |
| title_fullStr | Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria |
| title_full_unstemmed | Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria |
| title_short | Halogenated 3-Nitro-2<i>H</i>-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria |
| title_sort | halogenated 3 nitro 2 i h i chromenes as potential agents against multidrug resistant bacteria |
| topic | chromenes nitro derivatives antibacterial MDR bacteria halogenated drugs |
| url | https://www.mdpi.com/2079-6382/14/3/218 |
| work_keys_str_mv | AT patriciaicgodinho halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria AT paulaperezramos halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria AT yaizagabasa halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria AT enmanuelcornielle halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria AT saramsoto halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria AT raquelgsoengas halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria AT arturmssilva halogenated3nitro2ihichromenesaspotentialagentsagainstmultidrugresistantbacteria |