Synthesis, conformational studies, and biological properties of phosphonomethoxyethyl derivatives of nucleobases with a locked conformation via a pyrrolidine ring
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F15%3A00444048" target="_blank" >RIV/61388963:_____/15:00444048 - isvavai.cz</a>
Result on the web
<a href="http://pubs.rsc.org/en/content/articlepdf/2015/ob/c5ob00097a" target="_blank" >http://pubs.rsc.org/en/content/articlepdf/2015/ob/c5ob00097a</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c5ob00097a" target="_blank" >10.1039/c5ob00097a</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis, conformational studies, and biological properties of phosphonomethoxyethyl derivatives of nucleobases with a locked conformation via a pyrrolidine ring
Original language description
Systematic structure-activity studies on a diverse family of nucleoside phosphonic acids has led to the development of potent antiviral drugs such as HPMPC (CidofovirTM), PMEA (AdefovirTM), and PMPA (TenofovirTM), which are used in the treatment of CMV-induced retinitis, hepatitis B, and HIV, respectively. Here, we present the synthesis of a novel class of acyclic phosphonate nucleotides that have a locked conformation via a pyrrolidine ring. NMR analysis of these compounds revealed that the pyrrolidinering has a constrained conformation when in the cis-form at pD < 10 via hydrogen bonding. Four of these compounds were tested as inhibitors of the human and Plasmodium falciparum 6-oxopurine phosphoribosyltransferases. The most potent has a (K)i of 0.6mu M for Plasmodium falciparum HGXPRT.
Czech name
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Czech description
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Classification
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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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic & Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
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Volume of the periodical
13
Issue of the periodical within the volume
16
Country of publishing house
GB - UNITED KINGDOM
Number of pages
13
Pages from-to
4693-4705
UT code for WoS article
000353288700013
EID of the result in the Scopus database
2-s2.0-84927638050