Asset Details
Do you wish to reserve the book?
Enantiopure Indolo2,3-aquinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists
Hey, we have placed the reservation for you!
By the way, why not check out events that you can attend while you pick your title.
Oops! Something went wrong.
Looks like we were not able to place the reservation. Kindly try again later.
Are you sure you want to remove the book from the shelf?
Enantiopure Indolo2,3-aquinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists
Do you wish to request the book?
Enantiopure Indolo2,3-aquinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists
Please be aware that the book you have requested cannot be checked out. If you would like to checkout this book, you can reserve another copy
We have requested the book for you!
Your request is successful and it will be processed during the Library working hours. Please check the status of your request in My Requests.
Oops! Something went wrong.
Looks like we were not able to place your request. Kindly try again later.
Journal Article
Enantiopure Indolo2,3-aquinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists
2016
Overview
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 -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.
Publisher
MDPI,MDPI AG
Subject
/ Indoles - chemical synthesis
/ Ligands
/ Quinolizidines - chemical synthesis
/ Quinolizidines - pharmacology
/ Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors
/ Small Molecule Libraries - chemical synthesis
/ Small Molecule Libraries - chemistry
/ Small Molecule Libraries - pharmacology
