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Novel CGRP receptor antagonists from central amide replacements causing a reversal of preferred chirality
A previously utilized quinoline-for-N-phenylamide replacement strategy was employed against a central amide in a novel class of CGRP receptor antagonists. A unique and unexpected substitution pattern was ultimately required to maintain reasonable affinity for the CGRP receptor, while at the same tim...
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Published in: | Bioorganic & medicinal chemistry letters 2010-11, Vol.20 (22), p.6827-6830 |
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container_end_page | 6830 |
container_issue | 22 |
container_start_page | 6827 |
container_title | Bioorganic & medicinal chemistry letters |
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creator | Wood, Michael R. Schirripa, Kathy M. Kim, June J. Bednar, Rodney A. Fay, John F. Bruno, Joseph G. Moore, Eric L. Mosser, Scott D. Roller, Shane Salvatore, Christopher A. Vacca, Joseph P. Selnick, Harold G. |
description | A previously utilized quinoline-for-N-phenylamide replacement strategy was employed against a central amide in a novel class of CGRP receptor antagonists. A unique and unexpected substitution pattern was ultimately required to maintain reasonable affinity for the CGRP receptor, while at the same time predicting acceptable heterocycle positioning for related analogs. Subsequently, specific quinoline and naphthyridine compounds were prepared which supported these structural predictions by displaying CGRP binding affinities in the 0.037–0.15nM range. |
doi_str_mv | 10.1016/j.bmcl.2010.08.105 |
format | article |
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subjects | Amides - chemistry Amides - pharmacology Antagonist Biological and medical sciences Calcitonin gene-related peptide CGRP Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Receptors, Calcitonin Gene-Related Peptide - antagonists & inhibitors Stereoisomerism |
title | Novel CGRP receptor antagonists from central amide replacements causing a reversal of preferred chirality |
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