1360734-87-7Relevant academic research and scientific papers
Enantiopure indolo[2,3-a]quinolizidines: Synthesis and evaluation as NMDA receptor antagonists
Pereira, Nuno A. L.,Sureda, Francesc X.,Pérez, Maria,Amat, Mercedes,Santos, Maria M. M.
, (2016)
Enantiopure tryptophanol is easily obtained from the reduction of its parent natural amino acid trypthophan (available from the chiral pool), and can be used as chiral auxiliary/inductor to control the stereochemical course of a diastereoselective reaction. Furthermore, enantiopure tryptophanol is useful for the syntheses of natural products or biological active molecules containing the aminoalcohol functionality. In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity as N-Methyl D-Aspartate (NMDA) receptor antagonists. The indolo[2,3-a]quinolizidine scaffold was obtained using the following key steps: (i) a stereoselective cyclocondensation of (S)- or (R)-tryptophanol with appropriate racemic δ-oxoesters; (ii) a stereocontrolled cyclization on the indole nucleus. The synthesized enantiopure indolo[2,3-a]quinolizidines were evaluated as NMDA receptor antagonists and one compound was identified to be 2.9-fold more potent as NMDA receptor blocker than amantadine (used in the clinic for Parkinson's disease). This compound represents a hit compound for the development of novel NMDA receptor antagonists with potential applications in neurodegenerative disorders associated with overactivation of NMDA receptors.
Synthesis and evaluation of a novel series of indoloisoquinolines as small molecule anti-malarial leads
Horrocks, Paul,Fallon, Samantha,Denman, Laura,Devine, Oliver,Duffy, Liam J.,Harper, Anthony,Meredith, Emma-Louise,Hasenkamp, Sandra,Sidaway, Adam,Monnery, Daniel,Phillips, Theresa R.,Allin, Steven M.
supporting information; experimental part, p. 1770 - 1773 (2012/04/04)
A group of novel synthetic indoloisoquinolines was prepared and its potential as a novel series of smallmolecule anti-malarial leads was assessed. The structure-activity relationship on variation of three distinct regions of chemical space was investigate
