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    
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.
L J Hronowski; W A Szarek
Related Documents :
9719477 - Vincristine saturation of cellular binding sites and its cytotoxic activity in human ly...
6795547 - Ascorbic acid enhances the cytotoxic effect of 6-hydroxydopamine for human neuroblastom...
20043067 - Tranilast strongly sensitizes pancreatic cancer cells to gemcitabine via decreasing pro...
15878357 - Artelastin is a cytotoxic prenylated flavone that disturbs microtubules and interferes ...
15905177 - Headgroup-specific exposure of phospholipids in abca1-expressing cells.
12028437 - Role of membrane-bound heparin-binding epidermal growth factor-like growth factor (hb-e...
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    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Antineoplastic Agents / chemical synthesis*
Cells, Cultured
Chemical Phenomena
Fluorouracil / pharmacology
Heterocyclic Compounds / chemical synthesis,  pharmacology
Neoplasms, Experimental / drug therapy
Pyrimidine Nucleosides / chemical synthesis*,  pharmacology
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

Previous Document:  Inhibition by 5-(substituted-benzyl)-2,4-diaminopyrimidines of murine tumor (L5178Y) cell cultures s...
Next Document:  Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropyl...