Carbocyclic analogues of inosine-5'-monophosphate: synthesis and biological activity

E S Matyugina; S N Andreevskaya; T G Smirnova; A L Khandazhinskaya

Carbocyclic analogues of inosine-5'-monophosphate: synthesis and biological activity

Acta Naturae. 2012 Oct;4(4):73-7.

Authors

E S Matyugina¹, S N Andreevskaya, T G Smirnova, A L Khandazhinskaya

Affiliation

¹ Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str., 32, Moscow, Russia, 119991.

PMID: 23346382
PMCID: PMC3549521

Abstract

9-(4'-Phosphonomethoxy-2'-cyclopenten-1'-yl)hypoxanthine and 9-(4'-phosphonomethoxy-2',3'-dihydroxycyclopenten-1'-yl)hypoxanthine were synthesized as isosteric carbocyclic analogues of inosine-5'-monophosphate. The synthesized compounds were shown to be capable of inhibiting the activity of human type II inosine-5'-monophosphate dehydrogenase (IMPDH II) (IC(50 )= 500 µM) and to have no significant effects on the growth ofMycobacterium tuberculosis.

Keywords: Carbocyclic nucleosides; competitive inhibition; human IMPDH II,Mycobacterium tuberculosis; inosine-5’-monophosphate.