Document Detail

Cyclization-activated prodrugs. Basic esters of 5-bromo-2'-deoxyuridine.
MedLine Citation:
PMID:  2391697     Owner:  NLM     Status:  MEDLINE    
Some 3'- and 5'-[[(alkylamino)ethyl]glycyl] esters of 5-bromo-2'-deoxyuridine were prepared and evaluated in vitro as progenitors of the parent alcohol. The esters proved to be relatively stable at low pH but released 5-bromo-2'-deoxyuridine cleanly at rates which were pH and structure dependent. These basic esters are examples of cyclization-activated prodrugs in which generation of active drug is not linked to enzymatic cleavage but rather results from an intramolecular cyclization-elimination reaction.
W S Saari; J E Schwering; P A Lyle; S J Smith; E L Engelhardt
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  33     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1990 Sep 
Date Detail:
Created Date:  1990-10-04     Completed Date:  1990-10-04     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  2590-5     Citation Subset:  IM    
Merck Sharp & Dohme Research Laboratories, West Point, Pennsylvania 19486.
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MeSH Terms
Bromodeoxyuridine / analogs & derivatives*
Chemical Phenomena
Prodrugs / chemical synthesis*,  pharmacokinetics
Structure-Activity Relationship
Reg. No./Substance:
0/Esters; 0/Prodrugs; 59-14-3/Bromodeoxyuridine

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