Utilization of 1,3-Dioxolanes in the Synthesis of alpha-branched Alkyl and Aryl 9-[2-(Phosphonomethoxy)Ethyl]Purines and Study of the Influence of alpha-branched Substitution for Potential Biological Activity
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00504619" target="_blank" >RIV/61388963:_____/19:00504619 - isvavai.cz</a>
Alternative codes found
RIV/68378271:_____/19:00505072
Result on the web
<a href="https://www.tandfonline.com/doi/full/10.1080/15257770.2018.1506884" target="_blank" >https://www.tandfonline.com/doi/full/10.1080/15257770.2018.1506884</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1080/15257770.2018.1506884" target="_blank" >10.1080/15257770.2018.1506884</a>
Alternative languages
Result language
angličtina
Original language name
Utilization of 1,3-Dioxolanes in the Synthesis of alpha-branched Alkyl and Aryl 9-[2-(Phosphonomethoxy)Ethyl]Purines and Study of the Influence of alpha-branched Substitution for Potential Biological Activity
Original language description
Syntheses of alpha-branched alkyl and aryl substituted 9-[2-(phosphonomethoxy)ethyl]purines from substituted 1,3-dioxolanes have been developed. Key synthetic precursors, alpha-substituted dialkyl [(2-hydroxyethoxy)methyl]phosphonates were prepared via Lewis acid mediated cleavage of 1,3-dioxolanes followed by reaction with dialkyl or trialkyl phosphites. The best preparative yields were achieved under conditions utilizing tin tetrachloride as Lewis acid and triisopropyl phosphite. Attachment of purine bases to dialkyl [(2-hydroxyethoxy)methyl]phosphonates was performed by Mitsunobu reaction. Final alpha-branched 9-[2-(phosphonomethoxy)ethyl]purines were tested for antiviral, cytostatic and antiparasitic activity, the latter one determined as inhibitory activity towards Plasmodium falciparum enzyme hypoxanthine-guanine-xanthine phosphoribosyltransfesase. In most cases biological activity was only marginal.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA14-00522S" target="_blank" >GA14-00522S: Syntheses of new prodrug forms of biologically active nucleotide analogues</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Nucleosides Nucleotides & Nucleic Acids
ISSN
1525-7770
e-ISSN
—
Volume of the periodical
38
Issue of the periodical within the volume
2
Country of publishing house
US - UNITED STATES
Number of pages
38
Pages from-to
119-156
UT code for WoS article
000466612800001
EID of the result in the Scopus database
2-s2.0-85058183017