5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F14%3A00432303" target="_blank" >RIV/61388963:_____/14:00432303 - isvavai.cz</a>
Alternative codes found
RIV/68378041:_____/14:00432303 RIV/00216208:11140/14:10296018
Result on the web
<a href="http://dx.doi.org/10.1007/s00044-014-1018-9" target="_blank" >http://dx.doi.org/10.1007/s00044-014-1018-9</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1007/s00044-014-1018-9" target="_blank" >10.1007/s00044-014-1018-9</a>

Result language
angličtina
Original language name
5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production
Original language description
A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC (50) of 2 A mu M (higher activity than the most potent reference compound) while the IC (50)s of other derivatives were within the range of 9-36 A mu M. T
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GAP303%2F12%2F0172" target="_blank" >GAP303/12/0172: Structure-activity relationship (SAR) study of immunosuppressive effects of pyrimidine analogues</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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