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
Identifikátory výsledku
Kód výsledku v 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>
Nalezeny alternativní kódy
RIV/68378271:_____/19:00505072
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
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
Popis výsledku v původním jazyce
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.
Název v anglickém jazyce
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
Popis výsledku anglicky
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.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/GA14-00522S" target="_blank" >GA14-00522S: Syntézy nových prolékových forem biologicky aktivních nukleotidových analogů</a><br>
Návaznosti
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Ostatní
Rok uplatnění
2019
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Nucleosides Nucleotides & Nucleic Acids
ISSN
1525-7770
e-ISSN
—
Svazek periodika
38
Číslo periodika v rámci svazku
2
Stát vydavatele periodika
US - Spojené státy americké
Počet stran výsledku
38
Strana od-do
119-156
Kód UT WoS článku
000466612800001
EID výsledku v databázi Scopus
2-s2.0-85058183017