Synthesis and Biological Activity of Enantiomers of Antitumor Irofulven

Stereoselective synthesis of (−)-irofulven has been achieved by cycloaddition of (R)-5-chloro-5-methyl-2-cyclopentenone to the 1,3-dipolar intermediate from 1-acetyl-1-(diazoacetyl)cyclopropane. The enantiomer, (+)-irofulven, was prepared in a similar way starting with (S)-5-chloro-5-methyl-2-cyclop...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-02, Vol.69 (3), p.619-623
Main Authors: McMorris, Trevor C, Staake, Michael D, Kelner, Michael J
Format: Article
Language:English
Subjects:
Acylation
Adenocarcinoma - drug therapy
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Animals
Antineoplastic Agents, Alkylating - chemical synthesis
Antineoplastic Agents, Alkylating - chemistry
Antineoplastic Agents, Alkylating - pharmacology
Cell Line, Tumor
Chemistry
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Exact sciences and technology
Mice
Molecular Structure
Organic chemistry
Preparations and properties
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Stereoisomerism
Structure-Activity Relationship
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Summary:Stereoselective synthesis of (−)-irofulven has been achieved by cycloaddition of (R)-5-chloro-5-methyl-2-cyclopentenone to the 1,3-dipolar intermediate from 1-acetyl-1-(diazoacetyl)cyclopropane. The enantiomer, (+)-irofulven, was prepared in a similar way starting with (S)-5-chloro-5-methyl-2-cyclopentenone. (+)-Irofulven was 5 to 6 times less toxic than (−)-irofulven to adenocarcinoma (MV 522) cells.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo035084j