Issue 5, 2010
From the journal:

Organic & Biomolecular Chemistry

Dynamic combinatorial chemistry with hydrazones: libraries incorporating heterocyclic and steroidal motifs†

Mark G. Simpson,a   Michael Pittelkow,‡*a   Stephen P. Watsonb  and  Jeremy K. M. Sanders*a  

* Corresponding authors

a University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, United Kingdom
E-mail: jkms@cam.ac.uk
Fax: +44 1223 336017
Tel: +44 1223 336411

b Glaxo Wellcome Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, United Kingdom

Abstract

We expand the possibilities in hydrazone based dynamic combinatorial chemistry with a series of new building blocks incorporating heterocyclic motifs. The synthetic procedure allows efficient access to building blocks with the general structure (MeO)2CH-Heterocycle-C(O)NHNH2, originating from heterocycles with an amine and an ester functionality. The equilibrium distribution of macrocyclic N-acyl hydrazones formed upon deprotection of the building blocks with TFA in organic solvents is reported. The mixing behaviour of these heterocycle-based building blocks with our cholate-based building blocks is described, particularly the observation of kinetic intermediates that disappear following ‘proof-reading’.

Graphical abstract: Dynamic combinatorial chemistry with hydrazones: libraries incorporating heterocyclic and steroidal motifs

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Article information

DOI
https://doi.org/10.1039/B917146K
Article type
Paper
Submitted
19 Aug 2009
Accepted
20 Nov 2009
First published
11 Jan 2010

Org. Biomol. Chem., 2010,8, 1181-1187

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Dynamic combinatorial chemistry with hydrazones: libraries incorporating heterocyclic and steroidal motifs

M. G. Simpson, M. Pittelkow, S. P. Watson and J. K. M. Sanders, Org. Biomol. Chem., 2010, 8, 1181 DOI: 10.1039/B917146K

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