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TRPV1 modulators: Structure–activity relationships using a rational combinatorial approach

A discrete library of linear and hydantoin-containing dipeptide derivatives, based on the Lys-Trp(Nps) scaffold, was prepared by solid-phase synthesis. SAR studies indicated that potency for TRPV1 blockade and selectivity towards NMDA is mainly dictated by the side-chain length and the basic nature...

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Published in:	Bioorganic & medicinal chemistry letters 2011-06, Vol.21 (12), p.3541-3545
Main Authors:	Zaccaro, Laura, García-López, M. Teresa, González-Muñiz, Rosario, García-Martínez, Carolina, Ferrer-Montiel, Antonio, Albericio, Fernando, Royo, Miriam
Format:	Article
Language:	English
Subjects:	Analgesics antagonists Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Biological and medical sciences chemical derivatives Combinatorial Chemistry Techniques Combinatorial library Dipeptides Dipeptides - chemistry Humans Hydantoins Hydantoins - chemistry Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology ion channels lysine Medical sciences Molecular Structure Neuropharmacology Pharmacology. Drug treatments SAR studies Small Molecule Libraries - chemical synthesis Small Molecule Libraries - chemistry Small Molecule Libraries - pharmacology Structure-Activity Relationship structure-activity relationships TRPV Cation Channels - antagonists & inhibitors TRPV Cation Channels - drug effects TRPV1 tryptophan Tryptophan - chemical synthesis Tryptophan - chemistry Tryptophan - pharmacology
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description	A discrete library of linear and hydantoin-containing dipeptide derivatives, based on the Lys-Trp(Nps) scaffold, was prepared by solid-phase synthesis. SAR studies indicated that potency for TRPV1 blockade and selectivity towards NMDA is mainly dictated by the side-chain length and the basic nature of α, ω-groups in the N-terminal residue. The 2-Nps moiety at position 2 of Trp indole ring is preferred over the 2-pyridine one.
doi_str_mv	10.1016/j.bmcl.2011.04.141
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Drug treatments ; SAR studies ; Small Molecule Libraries - chemical synthesis ; Small Molecule Libraries - chemistry ; Small Molecule Libraries - pharmacology ; Structure-Activity Relationship ; structure-activity relationships ; TRPV Cation Channels - antagonists & inhibitors ; TRPV Cation Channels - drug effects ; TRPV1 ; tryptophan ; Tryptophan - chemical synthesis ; Tryptophan - chemistry ; Tryptophan - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-06, Vol.21 (12), p.3541-3545</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. 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subjects	Analgesics antagonists Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Biological and medical sciences chemical derivatives Combinatorial Chemistry Techniques Combinatorial library Dipeptides Dipeptides - chemistry Humans Hydantoins Hydantoins - chemistry Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology ion channels lysine Medical sciences Molecular Structure Neuropharmacology Pharmacology. Drug treatments SAR studies Small Molecule Libraries - chemical synthesis Small Molecule Libraries - chemistry Small Molecule Libraries - pharmacology Structure-Activity Relationship structure-activity relationships TRPV Cation Channels - antagonists & inhibitors TRPV Cation Channels - drug effects TRPV1 tryptophan Tryptophan - chemical synthesis Tryptophan - chemistry Tryptophan - pharmacology
title	TRPV1 modulators: Structure–activity relationships using a rational combinatorial approach
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