Access to a Structurally Complex Compound Collection via Ring Distortion of the Alkaloid Sinomenine

Many compound collections used in high-throughput screening are composed of members whose structural complexity is considerably lower than that of natural products. We previously reported a strategy for the synthesis of complex and diverse small molecules from natural products using ring-distortion...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 19; pp. 4852 - 4855
Main Authors Garcia, Alfredo, Drown, Bryon S, Hergenrother, Paul J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.10.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry Techniques, Synthetic - methods
Chemistry, Organic
Drug Design
Molecular Structure
Morphinans - chemistry
Morphinans - isolation & purification
Physical Sciences
Science & Technology
Sinomenium - chemistry
Small Molecule Libraries - chemical synthesis
Small Molecule Libraries - chemistry
Stereoisomerism
SMALL-MOLECULE INHIBITORS
NATURAL-PRODUCTS
MODULATORS
STRATEGY
PROTEIN-PROTEIN INTERACTIONS
DIVERSE COMPOUNDS
PRODUCT-LIKE SCAFFOLDS
DERIVATIVES
DISCOVERY
ORIENTED SYNTHESIS
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Summary:Many compound collections used in high-throughput screening are composed of members whose structural complexity is considerably lower than that of natural products. We previously reported a strategy for the synthesis of complex and diverse small molecules from natural products using ring-distortion reactions, called complexity-to-diversity (CtD), and herein, CtD is applied in the synthesis of 16 diverse scaffolds and 65 total compounds from the alkaloid natural product sinomenine. Chemoinformatic analysis shows that these compounds possess complex ring systems and marked three-dimensionality.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02333