Synthesis and antifungal activity of functionalized 2,3-spirostane isomers

Invasive fungal infections are a major complication for individuals with compromised immune systems. One of the most significant challenges in the treatment of invasive fungal infections is the increased resistance of many organisms to widely used antifungals, making the development of novel antifun...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2011-05, Vol.21 (10), p.2826-2831
Main Authors: Upadhyay, Sunil Kumar, Creech, Clinton C., Bowdy, Katharine L., Stevens, Edwin D., Jursic, Branko S., Neumann, Donna M.
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal agents
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Antifungal compounds
antifungal properties
Aspergillus fumigatus
Aspergillus fumigatus - drug effects
Biological and medical sciences
Candida albicans
Candida albicans - drug effects
Candida glabrata
Candida glabrata - drug effects
Cryptococcus neoformans
Cryptococcus neoformans - drug effects
fungi
Fungi - drug effects
immune system
Isomerism
isomers
Medical sciences
Microbial Sensitivity Tests
Molecular Structure
Pharmacology. Drug treatments
saponins
Spirostanes
Spirostans - chemical synthesis
Spirostans - chemistry
Spirostans - pharmacology
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Summary:Invasive fungal infections are a major complication for individuals with compromised immune systems. One of the most significant challenges in the treatment of invasive fungal infections is the increased resistance of many organisms to widely used antifungals, making the development of novel antifungal agents essential. Many naturally occurring products have been found to be effective antimicrobial agents. In particular, saponins with spirostane glycosidic moieties—isolated from plant or marine species—have been shown to possess a range of antimicrobial properties. In this report, we outline a novel approach to the synthesis of a number of functionalized spirostane molecules that can be further used as building blocks for novel spirostane-linked glycosides and present results from the in vitro screenings of the antifungal potential of each derivative against four fungal species, including Candida albicans, Cryptococcus neoformans, Candida glabrata, and the filamentous fungus Aspergillus fumigatus.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2011.03.092