192389-40-5Relevant articles and documents
Stereoselective synthesis of trans-threo-trans-oligopyrrolidines: Potential agents for RNA cleavage
Arndt, Hans-Dieter,Welz, Ruediger,Mueller, Sabine,Ziemer, Burkhart,Koert, Ulrich
, p. 3945 - 3962 (2007/10/03)
The 2,5-trans-substituted oligopyrrolidines constitute a promising class of novel RNA-binding agents as well as potential building blocks for artificial anion channels. A convergent synthesis of terpyrrolidine 1 and pyrrolidino-THF-pyrrolidine 2 is reported, relying upon convergent coupling of 2,5-trans-pyrrolidinecarboxaldehydes through bridging alkyne units under Felkin-Anh control and subsequent closure of the central ring. After complete deprotection, the free polyamine products were isolated in excellent yield and purity. Crystal structure analyses of a terpyrrolidine and a pyrrolidino-THF-pyrrolidine documented their helical privileged conformations. The compounds were then screened for RNA cleavage activity. Unlike the only weakly active simple polyamines, p-nitrosulfonamide 33 was found to induce cleavage at mM concentrations under physiologically relevant conditions.
Stereoselective synthesis of a terpyrrolidine unit, a potential building block for anion recognition
Arndt, Hans-Dieter,Polborn, Kurt,Koert, Ulrich
, p. 3879 - 3882 (2007/10/03)
The first stereoselective synthesis of a trans-threo-trans-threo-trans terpyrrolidine was achieved. A bidirectional strategy involving double acetylide coupling of two trans-N-BOC-pyrrolidine-aldehydes 3, epimerisation-free hydrogenation and ring closure via a seven-membered cyclic sulfate gives access to the terpyrrolidine scaffold.