Document Detail


Synthesis and biological evaluation of novel pyrimidine nucleoside analogues of 1,4-oxathiane, 1,4-dithiane, and 1,4-dioxane.
MedLine Citation:
PMID:  7086837     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Nine pyrimidine nucleoside analogues, in which the group attached at N-1 is a six-membered ring containing two heteroatoms, have been synthesized using the Vorbrüggen and Bennua (Vorbrüggen, H.; Bennua, B. Tetrahedron Lett. 1978, 1339) coupling procedure. These are 1-(1,4-oxathian-3-yl)-5-fluorouracil (8), 1-(4-oxo-1,4-oxathian-3-yl)-5-fluorouracil (two stereoisomers 9 and 10, resolved by silica gel column chromatography, 1-(1,4-oxathian-3-yl)-5-fluorouracil (11), 1-(1,4-oxathian-2-yl)-5-fluorouracil (12), 1-(1,4-dithin-2-yl)-5-flourouracil (15), 1-(1,4-dithian-2-yl)uracil (16), 1-(1,4-dithian-2-yl)thymine (17), and 1-(1,4-dioxan-2-yl)-5-fluorouracil (20). All of the analogous were tested for cell-growth inhibition using mouse and human tumor cell lines. The ID50 values of all of the analogues are greater than 10(-4) M, except in the case of 11 using the L1210 cell line. The most active analogues found are compounds 11 and 17, which were found to be 100 and 200 times less active, respectively, than 5-fluorouracil in the human erythroleukemia cell line, K-562.
Authors:
L J Hronowski; W A Szarek
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  25     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1982 May 
Date Detail:
Created Date:  1982-08-14     Completed Date:  1982-08-14     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:  522-6     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Animals
Antineoplastic Agents / chemical synthesis*
Cells, Cultured
Chemical Phenomena
Chemistry
Fluorouracil / pharmacology
Heterocyclic Compounds / chemical synthesis,  pharmacology
Humans
Mice
Neoplasms, Experimental / drug therapy
Pyrimidine Nucleosides / chemical synthesis*,  pharmacology
Chemical
Reg. No./Substance:
0/Antineoplastic Agents; 0/Heterocyclic Compounds; 0/Pyrimidine Nucleosides; 51-21-8/Fluorouracil

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


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