Toward Understanding How the Lactone Moiety of Discodermolide Affects Activity

A series of simplified discodermolide analogues have been designed and synthesized in an attempt to understand the role of the lactone ring. These synthetic efforts have led to an unsubstituted butyrolactone 9 being generated, which shows improved activity over the natural product.

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-05, Vol.127 (18), p.6532-6533
Main Authors: Shaw, Simon J, Sundermann, Kurt F, Burlingame, Mark A, Myles, David C, Freeze, B. Scott, Xian, Ming, Brouard, Ignacio, Smith, Amos B
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Alkanes - pharmacology
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biological and medical sciences
Carbamates - chemistry
Carbamates - pharmacology
Cell Line, Tumor
Drug Screening Assays, Antitumor
General pharmacology
Humans
Lactones - chemistry
Lactones - pharmacology
Medical sciences
Molecular Conformation
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Pyrones
Stereoisomerism
Structure-Activity Relationship
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Description
Summary:A series of simplified discodermolide analogues have been designed and synthesized in an attempt to understand the role of the lactone ring. These synthetic efforts have led to an unsubstituted butyrolactone 9 being generated, which shows improved activity over the natural product.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja051185i