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Synthesis of Novel N-9-Substituted Purine Derivatives from Polymer Supported alpha-Amino Acids

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F15%3A73576783" target="_blank" >RIV/61989592:15110/15:73576783 - isvavai.cz</a>

  • Alternative codes found

    RIV/61389030:_____/15:00447320 RIV/61989592:15310/15:73576783

  • Result on the web

    <a href="https://pubs.acs.org/doi/10.1021/acscombsci.5b00071" target="_blank" >https://pubs.acs.org/doi/10.1021/acscombsci.5b00071</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acscombsci.5b00071" target="_blank" >10.1021/acscombsci.5b00071</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Synthesis of Novel N-9-Substituted Purine Derivatives from Polymer Supported alpha-Amino Acids

  • Original language description

    Solid-phase synthesis of purine derivatives bearing an alpha-amino acid motif in position 9 is described herein. Polymer supported amines were acylated with various Fmoc-alpha-amino acids and, after cleavage of the protecting group, arylation with 4,6-dichloro-5-nitropyrimidine or 2,4-dichloro-5-nitropyrimidine was performed. The second chlorine atom was replaced with various amines. Subsequent reduction of the nitro group, followed by reaction with aldehydes, afforded the purine scaffold. After cleavage from the polymer support, the target compounds were obtained in very good crude purity, good overall yields, and excellent enantiomeric purity. The anticancer activity of prepared compounds was tested in vitro against human cancer cell lines MCF7 and K562, and they were found to have mild, but clear dose-dependent effects.

  • 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

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

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

    ACS Combinatorial Science

  • ISSN

    2156-8952

  • e-ISSN

  • Volume of the periodical

    17

  • Issue of the periodical within the volume

    7

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    7

  • Pages from-to

    426-432

  • UT code for WoS article

    000358026300007

  • EID of the result in the Scopus database

    2-s2.0-84953884030