Document Detail


Regio- and stereospecific synthesis of mono-beta-d-glucuronic acid derivatives of combretastatin A-1.
MedLine Citation:
PMID:  20496923     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-d-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.
Authors:
Rajendra P Tanpure; Tracy E Strecker; David J Chaplin; Bronwyn G Siim; Mary Lynn Trawick; Kevin G Pinney
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Journal of natural products     Volume:  73     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2010 Jun 
Date Detail:
Created Date:  2010-06-25     Completed Date:  2010-07-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1093-101     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, TX 76798-7348, USA.
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MeSH Terms
Descriptor/Qualifier:
Antineoplastic Agents, Phytogenic / chemical synthesis*,  chemistry,  pharmacology
Drug Screening Assays, Antitumor
Glucuronic Acid / chemical synthesis*,  chemistry*,  pharmacology
Humans
Molecular Structure
Stereoisomerism
Stilbenes / chemical synthesis*,  chemistry*,  pharmacology
Chemical
Reg. No./Substance:
0/Antineoplastic Agents, Phytogenic; 0/Stilbenes; 109971-63-3/combretastatin A-1; 576-37-4/Glucuronic Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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