Viridin analogs derived from steroidal building blocks

Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-11, Vol.22 (22), p.6919-6922
Main Authors: Viswanathan, Kishore, Ononye, Sophia N., Cooper, Harold D., Kyle Hadden, M., Anderson, Amy C., Wright, Dennis L.
Format: Article
Language:English
Subjects:
Androstadienes - chemistry
Androstenes - chemical synthesis
Androstenes - chemistry
Androstenes - toxicity
Bacteriocins - chemical synthesis
Bacteriocins - chemistry
Bacteriocins - toxicity
Binding Sites
Biological and medical sciences
breast neoplasms
Breast Neoplasms - metabolism
Breast Neoplasms - pathology
Cell Survival - drug effects
chemistry
Crystallography, X-Ray
electrophysiology
enzyme inhibitors
feedstocks
Female
Humans
Irreversible enzyme inhibitors
MCF-7 Cells
Medical sciences
Pharmacology. Drug treatments
Phosphatidylinositol 3-Kinases - antagonists & inhibitors
Phosphatidylinositol 3-Kinases - metabolism
PI-3K
Protein Kinase Inhibitors - chemical synthesis
Protein Kinase Inhibitors - chemistry
Protein Kinase Inhibitors - toxicity
Protein Structure, Tertiary
Steroid
steroids
Steroids - chemistry
Viridin
Wortmannin
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Description
Summary:Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe the synthesis of viridin/wortmannin hybrid molecules from readily available building blocks that function as PI-3K inhibitors and maintain their electrophilic properties. The compounds also show anti-proliferative effects against a breast cancer line.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.09.015