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Issue 5, 2010
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Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

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Abstract

We describe an efficient and general strategy for the synthesis of dimethyl acetal functionalised steroidal hydrazides based on the cholic acid skeleton with the aim of using these compounds as building blocks for dynamic combinatorial chemistry. Deprotection of the acetal protected building blocks with TFA leads to formation of libraries containing macrocyclic N-acyl hydrazone oligomers. The isolation of several of these, and their characterisation using NMR is described. The effects on the equilibrium library distribution by varying the substituents at C-7 and C-12, extending the side-chain with glycine, and inverting the configuration at C-3 are discussed. Finally, we report the exchange properties of these macrocycles and demonstrate new examples of proof-reading and self-sorting in dynamic combinatorial libraries.

Graphical abstract: Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

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Supplementary files

Article information


Submitted
19 Aug 2009
Accepted
20 Nov 2009
First published
11 Jan 2010

Org. Biomol. Chem., 2010,8, 1173-1180
Article type
Paper

Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

M. G. Simpson, M. Pittelkow, S. P. Watson and J. K. M. Sanders, Org. Biomol. Chem., 2010, 8, 1173
DOI: 10.1039/B917145B

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