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...

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Bibliographic Details
Published in:International journal of molecular sciences 2019-04, Vol.20 (9), p.2121
Main Authors: Jastrzebska, Izabella, Mellea, Stefano, Salerno, Valerio, Grzes, Pawel Adam, Siergiejczyk, Leszek, Niemirowicz-Laskowska, Katarzyna, Bucki, Robert, Monti, Bonifacio, Santi, Claudio
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
antibacterial
Antibacterial activity
antibiofilm
Antibiotics
Antimicrobial agents
Bacteria
Biofilms
Biofilms - drug effects
Chlorides - chemistry
Clinical trials
Communication
Correlation
Diabetes mellitus
Homeostasis
Immunocompromised hosts
Investigations
Magnetic Resonance Spectroscopy
Molecular Structure
NMR
Non-small cell lung carcinoma
Nuclear magnetic resonance
Organoselenium Compounds - chemical synthesis
Organoselenium Compounds - chemistry
Organoselenium Compounds - pharmacology
Pseudomonas aeruginosa
Pseudomonas aeruginosa - drug effects
Selenium
Stereochemistry
steroids
Steroids - chemistry
Zinc Compounds - chemistry
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Summary: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 Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms20092121