181705-71-5Relevant academic research and scientific papers
Exploring the chiral space within the active site of α-thrombin with a constrained mimic of D-Phe-Pro-Arg - Design, synthesis, inhibitory activity, and X-ray structure of an enzyme-inhibitor complex
Hanessian, Stephen,Balaux, Elise,Musil, Djorde,Olsson, Lise-Lotte,Nilsson, Ingemar
, p. 243 - 247 (2007/10/03)
An indolizidinone motif with strategically placed substitutents was designed and synthesized as a constrained mimic of D-Phe-Pho-Arg. Low nanomolar inhibition of α-thrombin validates the design elements in this inhibitor which also exhibits a 20-fold selectivity for thrombin versus trypsin. An X-ray crystal structure of the inhibitor with α-thrombin shows the expected interactions with key amino acids within the active site and some notable changes in positions. (C) Elsevier Science Ltd. All rights reserved.
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.
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.
