N-4-Acyl derivatives as lipophilic prodrugs of cidofovir and its 5-azacytosine analogue, (S)-HPMP-5-azaC: Chemistry and antiviral activity

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F14%3A00428744" target="_blank" >RIV/61388963:_____/14:00428744 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.bmc.2014.03.031" target="_blank" >http://dx.doi.org/10.1016/j.bmc.2014.03.031</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.bmc.2014.03.031" target="_blank" >10.1016/j.bmc.2014.03.031</a>

Result language
angličtina
Original language name
N-4-Acyl derivatives as lipophilic prodrugs of cidofovir and its 5-azacytosine analogue, (S)-HPMP-5-azaC: Chemistry and antiviral activity
Original language description
Even number fatty acid residues-docosanoyl (behenoyl) and stearoyl were selected for introduction to the N-4-position of (S)-1-[3-hydroxy-2-(phosphonomethoxy) propyl] cytosine) (HPMPC, cidofovir), and its 5-azacytosine counterpart, (S)-1-[3-hydroxy-2-(phosphonomethoxy) propyl] cytosine) (HPMP-5-azaC) with the aim to prepare a new type of lipophilic prodrugs. The study on the influence of these modifications to the stability and biological activity of both antivirals was performed. Different reactivity of both systems towards acylation reactions was also found: the 4-NH2 group of cidofovir was more reactive compared to that of HPMP-5-azaC. In 5-azacytosine derivatives, we found mostly a destabilizing effect of the N-4-acylation but this could be compensated by a positive influence of the esterification of the phosphonate group. Chemical stability of the 5-azacytosine moiety in the HPMP series is increasing in the following order: HPMP-5-azaC < cyclic HPMP-5-azaC < HPMP-5-azaC esters. Fr
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
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Project
<a href="/en/project/FR-TI4%2F625" target="_blank" >FR-TI4/625: New derivatives of 5-azacytosine nucleosides like demethylating therapeutics: identification of clinical candidates and efficiency biomarkers.</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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