Dynamic combinatorial chemistry with hydrazones: libraries incorporating heterocyclic and steroidal motifs.
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'.
Simpson
Mark G
MG
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
Pittelkow
Michael
M
Watson
Stephen P
SP
Sanders
Jeremy K M
JK
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*
D006571:Heterocyclic Compounds; D006835:Hydrazones; D013256:Steroids