Oxolane Ammonium Salts (Muscarine-Like)-Synthesis and Microbiological Activity

Commercially available 2-deoxy-D-ribose was used to synthesize the appropriate oxolane derivative-(2 ,3 )-2-(hydroxymethyl)oxolan-3-ol-by reduction and dehydration/cyclization in an acidic aqueous solution. Its monotosyl derivative, as a result of the quaternization reaction, allowed us to obtain ei...

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Bibliographic Details
Published in:International journal of molecular sciences 2024-02, Vol.25 (4), p.2368
Main Authors: Bogdanowicz, Patrycja, Madaj, Janusz, Szweda, Piotr, Sikorski, Artur, Samaszko-Fiertek, Justyna, Dmochowska, Barbara
Format: Article
Language:English
Subjects:
2-deoxy-D-ribose
Ammonium Compounds
Ammonium paratungstate
ammonium salts
Analysis
Anti-Bacterial Agents - chemistry
Biological activity
Carbon
Chloride
Crystals
Hydrogen bonds
Microbial Sensitivity Tests
microbiological tests
Microbiology
Monosaccharides
Muscarine
Nitrogen
oxolane ring
Pharmaceutical industry
Salts - pharmacology
Structure
Sugars
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Summary:Commercially available 2-deoxy-D-ribose was used to synthesize the appropriate oxolane derivative-(2 ,3 )-2-(hydroxymethyl)oxolan-3-ol-by reduction and dehydration/cyclization in an acidic aqueous solution. Its monotosyl derivative, as a result of the quaternization reaction, allowed us to obtain eight new muscarine-type derivatives containing a quaternary nitrogen atom and a hydroxyl group linked to the oxolane ring. Their structure was fully confirmed by the results of NMR, MS and IR analyses. The crystal structure of the pyridinium derivative showed a high similarity of the conformation of the oxolane ring to previously published crystal structures of muscarine. Two reference strains of Gram-negative bacteria ( ATCC 25922 and ATCC 27853), two reference strains of Gram-positive staphylococci ( ATCC 25923 and ATCC 29213) and four reference strains of pathogenic yeasts of the genus spp. ( SC5314, DSM 11226, DSM 6128 and DSM 5784) were selected for the evaluation of the antimicrobial potential of the synthesized compounds. The derivative containing the longest (decyl) chain attached to the quaternary nitrogen atom turned out to be the most active.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms25042368