title: Dynamic combinatorial chemistry with hydrazones: libraries incorporating heterocyclic and steroidal motifs.
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)(2)CH-Heterocycle-C(O)NHNH(2), 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'.
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
authors.forename: Mark G
authors.initials: MG
authors.lastname: Simpson
authors.forename: Michael
authors.initials: M
authors.lastname: Pittelkow
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Watson
authors.forename: Jeremy K M
authors.initials: JK
authors.lastname: Sanders
mesh_terms: D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013256:Steroids / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D006835:Hydrazones; D013256:Steroids