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

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

E S Matyugina  1 , S N Andreevskaya, T G Smirnova, A L Khandazhinskaya
Affiliations

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

E S Matyugina et al. Acta Naturae. 2012 Oct.

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.

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Figures

Fig. 1
Fig. 1
Inosine-5’-monophosphate and its isosteric carbocyclic analogues
Scheme
Scheme
a – Ethanol (pure), K 2 CO 3 , refluxing for 1 hour; b – NaH, TosOCH 2 P(O)OC 2 H 5 OH, Cs 2 CO 3 , DMF; c – OsO 4 , NMMO, dioxane; d - (CH 3 ) 3 SiBr, DMF
Fig. 2
Fig. 2
Dose-dependent inhibition of IMPDH II by compounds 1 and 2
See this image and copyright information in PMC

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