2306252-57-1Relevant articles and documents
Synthesis and differential functionalisation of pyrrolidine and piperidine based spirodiamine scaffolds
Weinberg, Kamil,Stoit, Axel,Kruse, Chris G.,Haddow, Mairi F.,Gallagher, Timothy
, p. 4694 - 4707 (2013/07/04)
The synthesis and differential substitution/protection of a series of spirodiamine scaffolds are described. Methods for selective access to the two mono-N-methyl isomers based on 2,7-diazaspiro[4.5]decane are also described. Key precursors associated with this chemistry are prone to rearrangement and methods for circumventing this issue are reported. While direct mono-carbamoylation (Boc) was not efficient, selective deprotection of doubly Boc-protected derivatives derived from symmetrical diamines provided mono-Boc variants. N-Arylation, exemplified by a series of monosubstituted spirodiamines incorporating the 2-chloro-5-pyridyl moiety, which is a privileged nicotinic agonist substructure, has also been carried out to provide monoarylated secondary and tertiary spirodiamines variants.
Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors
Sippy, Kevin B.,Anderson, David J.,Bunnelle, William H.,Hutchins, Charles W.,Schrimpf, Michael R.
scheme or table, p. 1682 - 1685 (2009/11/30)
Several N-pyridin-3-yl spirobicyclic diamines, designed as conformationally restricted analogs of tebanicline (ABT-594), were synthesized as novel ligands for nicotinic acetylcholine receptors (nAChR). The spirocyclic compounds exhibited weaker binding affinity, than other constrained analogs in accord with a pharmacophore model. Nevertheless, some (1a, 1b) possessed (partial) agonist potencies comparable to nicotine at the α4β2 subtype, but with greatly improved selectivity relative to the α3β4* nAChR.