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

Michael Pittelkow; Jeremy K. M. Sanders; Mark G. Simpson; Stephen P. Watson

doi:10.1039/b917146k

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

Michael Pittelkow, Jeremy K. M. Sanders, Mark G. Simpson, Stephen P. Watson

Department of Chemistry

28 Citations (Scopus)

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'.

Original language	English
Journal	Organic & Biomolecular Chemistry
Pages (from-to)	1181-1187
Number of pages	7
ISSN	1477-0520
DOIs	https://doi.org/10.1039/b917146k
Publication status	Published - 11 Jan 2010

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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'.",

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AU - Watson, Stephen P.

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N2 - 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'.

AB - 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'.

U2 - 10.1039/b917146k

DO - 10.1039/b917146k

M3 - Journal article

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

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

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