Issue 23, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 3-(carboxyarylalkyl)imidazo[2,1-f][1,2,4]triazines as potential inhibitors of AMP deaminase†

Joseph K. Kirkman,a   Stephen D. Lindell,*b   Simon Maechling,b   Alexandra M. Z. Slawinc  and  Christopher J. Moody*ad  

* Corresponding authors

a Department of Chemistry, School of Biological and Chemical Sciences, University of Exeter, Stocker Road, Exeter, U.K.

b Bayer CropScience AG, Werk Höchst, G836, Frankfurt am Main, Germany
E-mail: stephen.lindell@bayercropscience.com

c School of Chemistry, University of St. Andrews, Fife, Scotland, U.K.

d School of Chemistry, University of Nottingham, University Park, Nottingham, U.K.
E-mail: c.j.moody@nottingham.ac.uk

Abstract

C-Ribosyl 1,2,4-triazolo[1,2,4]triazines which are able to undergo covalent hydration are of interest as potential inhibitors of AMP deaminase. In a search for compounds with improved bioavailability we have synthesized compounds in which the sugar has been replaced by carboxyarylalkyl based ribose phosphate mimics. The target carboxyarylalkyl imidazotriazines 11 and 12 were synthesized using a linear seven step sequence starting from simple benzoate derivatives. Alternatively, the hydroxyethyl imidazotriazine 39 is available in five steps and this synthon was used to prepare the imidazotriazines 34 and 48 in a short convergent manner.

Graphical abstract: Synthesis of 3-(carboxyarylalkyl)imidazo[2,1-f][1,2,4]triazines as potential inhibitors of AMP deaminase

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Article information

DOI
https://doi.org/10.1039/B810850A
Article type
Paper
Submitted
25 Jun 2008
Accepted
09 Sep 2008
First published
22 Oct 2008

Org. Biomol. Chem., 2008,6, 4452-4459

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Synthesis of 3-(carboxyarylalkyl)imidazo[2,1-f][1,2,4]triazines as potential inhibitors of AMP deaminase

J. K. Kirkman, S. D. Lindell, S. Maechling, A. M. Z. Slawin and C. J. Moody, Org. Biomol. Chem., 2008, 6, 4452 DOI: 10.1039/B810850A

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