Document Detail

Antineoplastic agents 460. Synthesis of combretastatin A-2 prodrugs.
MedLine Citation:
PMID:  12049477     Owner:  NLM     Status:  MEDLINE    
The original synthesis of combretastatin A-2 (1a) was modified to provide an efficient scale-up procedure for obtaining this antineoplastic stilbene. Subsequent conversion to a useful prodrug was accomplished by phosphorylation employing in situ formation of dibenzylchlorophosphite followed by cleavage of the benzyl ester protective groups with bromotrimethylsilane to afford the phosphoric acid intermediate 11. The latter was immediately treated with sodium methoxide to complete a practical route to the disodium phosphate prodrug (2a). The phosphoric acid precursor (11) of phosphate 2a was employed in a parallel series of reactions to produce a selection of metal and ammonium cation prodrug candidates. Each of the phosphate salts (2a-q) was evaluated with respect to relative solubility behavior, cancer cell growth inhibition and antimicrobial activity.
G R Pettit; B R Moser; M R Boyd; J M Schmidt; R K Pettit; J C Chapuis
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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.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Anti-cancer drug design     Volume:  16     ISSN:  0266-9536     ISO Abbreviation:  Anticancer Drug Des.     Publication Date:    2001 Aug-Oct
Date Detail:
Created Date:  2002-06-06     Completed Date:  2002-06-19     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8603523     Medline TA:  Anticancer Drug Des     Country:  United States    
Other Details:
Languages:  eng     Pagination:  185-93     Citation Subset:  IM    
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe 85287-2404, USA.
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MeSH Terms
Antineoplastic Agents, Phytogenic / chemical synthesis*,  chemistry,  pharmacology
Bacteria / drug effects
Bibenzyls / chemical synthesis*,  chemistry,  pharmacology
Drug Design
Indicator Dilution Techniques
Indicators and Reagents
Microbial Sensitivity Tests
Neoplasms / metabolism
Phosphates / chemical synthesis,  chemistry
Prodrugs / chemical synthesis*,  chemistry,  pharmacology
Tumor Cells, Cultured
Grant Support
CA44344-05-12/CA/NCI NIH HHS
Reg. No./Substance:
0/Antineoplastic Agents, Phytogenic; 0/Bibenzyls; 0/Indicators and Reagents; 0/Phosphates; 0/Prodrugs; 0/Stilbenes; 82855-09-2/combretastatin

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