PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their ant...

Descripción completa

Detalles Bibliográficos
Autores principales: Jastrzebska, Izabella, Mellea, Stefano, Salerno, Valerio, Grzes, Pawel Adam, Siergiejczyk, Leszek, Niemirowicz-Laskowska, Katarzyna, Bucki, Robert, Monti, Bonifacio, Santi, Claudio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6539910/
https://www.ncbi.nlm.nih.gov/pubmed/31032813
http://dx.doi.org/10.3390/ijms20092121
_version_ 1783422501007654912
author Jastrzebska, Izabella
Mellea, Stefano
Salerno, Valerio
Grzes, Pawel Adam
Siergiejczyk, Leszek
Niemirowicz-Laskowska, Katarzyna
Bucki, Robert
Monti, Bonifacio
Santi, Claudio
author_facet Jastrzebska, Izabella
Mellea, Stefano
Salerno, Valerio
Grzes, Pawel Adam
Siergiejczyk, Leszek
Niemirowicz-Laskowska, Katarzyna
Bucki, Robert
Monti, Bonifacio
Santi, Claudio
author_sort Jastrzebska, Izabella
collection PubMed
description We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their antibacterial properties against multidrug-resistant bacteria, such as Pseudomonas aeruginosa Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation.
format Online
Article
Text
id pubmed-6539910
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-65399102019-06-04 PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity Jastrzebska, Izabella Mellea, Stefano Salerno, Valerio Grzes, Pawel Adam Siergiejczyk, Leszek Niemirowicz-Laskowska, Katarzyna Bucki, Robert Monti, Bonifacio Santi, Claudio Int J Mol Sci Communication We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their antibacterial properties against multidrug-resistant bacteria, such as Pseudomonas aeruginosa Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation. MDPI 2019-04-29 /pmc/articles/PMC6539910/ /pubmed/31032813 http://dx.doi.org/10.3390/ijms20092121 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Jastrzebska, Izabella
Mellea, Stefano
Salerno, Valerio
Grzes, Pawel Adam
Siergiejczyk, Leszek
Niemirowicz-Laskowska, Katarzyna
Bucki, Robert
Monti, Bonifacio
Santi, Claudio
PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity
title PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity
title_full PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity
title_fullStr PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity
title_full_unstemmed PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity
title_short PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity
title_sort phsezncl in the synthesis of steroidal β-hydroxy-phenylselenides having antibacterial activity
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6539910/
https://www.ncbi.nlm.nih.gov/pubmed/31032813
http://dx.doi.org/10.3390/ijms20092121
work_keys_str_mv AT jastrzebskaizabella phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT melleastefano phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT salernovalerio phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT grzespaweladam phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT siergiejczykleszek phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT niemirowiczlaskowskakatarzyna phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT buckirobert phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT montibonifacio phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity
AT santiclaudio phseznclinthesynthesisofsteroidalbhydroxyphenylselenideshavingantibacterialactivity

Ejemplares similares