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Synthesis of New 5'-Norcarbocyclic Aza/Deaza Purine Fleximers - Noncompetitive Inhibitors of E.coli Purine Nucleoside Phosphorylase.


ABSTRACT: A new series of flexible 5'-norcarbocyclic aza/deaza-purine nucleoside analogs were synthesized from 6-oxybicyclo[3.1.0.]hex-2-ene and pyrazole-containing fleximer analogs of heterocyclic bases using the Trost procedure. The compounds were evaluated as potential inhibitors of E. coli purine nucleoside phosphorylase. Analog 1-3 were found to be noncompetitive inhibitors with inhibition constants of 14-24 mM. From the data obtained, it can be assumed that the new 5'-norcarbocyclic nucleoside analogs interact with the active site of the PNP like natural heterocyclic bases. But at the same time the presence of a cyclopentyl moiety with 2' and 3' hydroxyls is necessary for the inhibitory properties, since compounds 8-10, without those groups did not exhibit an inhibitory effect under the experimental conditions.

SUBMITTER: Khandazhinskaya A 

PROVIDER: S-EPMC9114674 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Synthesis of New 5'-Norcarbocyclic Aza/Deaza Purine Fleximers - Noncompetitive Inhibitors of <i>E.coli</i> Purine Nucleoside Phosphorylase.

Khandazhinskaya Anastasia A   Fateev Ilja I   Konstantinova Irina I   Esipov Roman R   Polyakov Konstantin K   Seley-Radtke Katherine K   Kochetkov Sergey S   Matyugina Elena E  

Frontiers in chemistry 20220504


A new series of flexible 5'-norcarbocyclic aza/deaza-purine nucleoside analogs were synthesized from 6-oxybicyclo[3.1.0.]hex-2-ene and pyrazole-containing fleximer analogs of heterocyclic bases using the Trost procedure. The compounds were evaluated as potential inhibitors of <i>E. coli</i> purine nucleoside phosphorylase. Analog <b>1-3</b> were found to be noncompetitive inhibitors with inhibition constants of 14-24 mM. From the data obtained, it can be assumed that the new 5'-norcarbocyclic nu  ...[more]

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