192389-43-8Relevant academic research and scientific papers
STRUCTURAL MIMETICS OF PROLINE-RICH PEPTIDES AND THE PHARMACEUTICAL USE THEREOF
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Page/Page column 21-22, (2011/02/26)
The invention relates to compounds of general formula (I), which can be used particularly as structural mimetics of proline-rich peptides and are therefore capable of binding PRM binding domains (proline-rich motif binding domains) of proteins. The invention also relates to the use of said compounds as pharmaceutical active agents and the use of these pharmaceutical active agents for treating bacterial diseases, neurodegenerative diseases and tumours.
One-pot cross-coupling of N-acyl N,O-acetals with α,β- unsaturated compounds
Xiang, Yong-Gang,Wang, Xiang-Wu,Zheng, Xiao,Ruan, Yuan-Ping,Huang, Pei-Qiang
supporting information; experimental part, p. 7045 - 7047 (2010/04/25)
The synergistic action of BF3·OEt2 and SmI2 allowed a series of intermolecular cross-couplings of readily available N-acyl N,O-acetals with α,β-unsaturated compounds to be performed in high yields, which was applied to the
Diastereoselective synthesis of 4,5′-bis-proline compounds via reductive dimerization of N-acyloxyiminium ions
Zanardi, Franca,Sartori, Andrea,Curti, Claudio,Battistini, Lucia,Rassu, Gloria,Nicastro, Giuseppe,Casiraghi, Giovanni
, p. 1814 - 1817 (2007/10/03)
A short, practical synthesis of novel, unsymmetrical 4,5′-bis-proline compounds has been achieved, highlighted by the application of an unprecedented samarium diiodide-driven regio- and diastereocontrolled reductive dimerization of N-acyloxyiminium ions generated from readily available 2-methoxy-5- silyloxymethyl-N-Boc pyrrolidines. The title proline dimers proved to be pertinent metal-free catalysts in aldol and Mannich reactions.
Stereoselective synthesis of 2,5-di- and 2,2,5-trisubstituted pyrrolidines by allylation reacton of acyliminium ion
Shinada, Tetsuro,Hamada, Makoto,Kawasaki, Masanori,Ohfune, Yasufumi
, p. 511 - 525 (2007/10/03)
-Allylation reactions of allytrimethylsilane and an allylcopper reagent to acyliminium ions derived from several 2-monosubstituted and 2,2-disubstituted pyrrolidinones were examined. These reactions proceeded in a stereoselective manner to give the corresponding allylated adducts. The stereochemical outcomes of these reactions were dependent upon the allylating reagents or the structures of the acyliminium ions.
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.
Synthesis of diversely functionalized indolizidinones and related bicyclic lactams using intramolecular Grubbs olefin metathesis and Dieckmann condensation
Hanessian, Stephen,Sailes, Helen,Munro, Alexander,Therrien, Eric
, p. 7219 - 7233 (2007/10/03)
Bicyclic 1-aza-2-oxo ring systems with versatile functionality were synthesized from the Grubbs olefin metathesis of appropriate olefinic precursors, starting with L-pyroglutamic acid. The carbocyclization products were further functionalized utilizing th
Lewis acid assisted vinylogous Mannich and Mukaiyama aldol reactions: A route to densely hydroxylated indolizidine alkaloid analogues
Rassu, Gloria,Carta, Paola,Pinna, Luigi,Battistini, Lucia,Zanardi, Franca,Acquotti, Domenico,Casiraghi, Giovanni
, p. 1395 - 1400 (2007/10/03)
The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine-australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)- glyceraldehyde 9.
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.
A versatile synthesis of a β-turn peptidomimetic scaffold: An approach towards a designed model antagonist of the tachykinin NK-2 receptor
Hanessian, Stephen,McNaughton-Smith, Grant
, p. 1567 - 1572 (2007/10/03)
A general and stereocontrolled synthesis of an azabicyclo[4.3.0]nonane amino acid template with an appended substitutent at C-5 was developed. The approach allows for stereochemical and functional variations that extend the utility of these rigid amino acid motifs as peptidomimetics. The synthesis of a weakly active but specific NK-2 receptor antagonist is described.
