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C2‐Modified Sparteine Derivatives Are a New Class of Potentially Long‐Acting Sodium Channel Blockers
Author(s) -
Gawali Vaibhavkumar S.,
Simeonov Svilen,
Drescher Martina,
Knott Thomas,
Scheel Olaf,
Kudolo John,
Kählig Hanspeter,
Hochenegg Ulla,
Roller Alexander,
Todt Hannes,
Maulide Nuno
Publication year - 2017
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201700568
Subject(s) - sparteine , alkaloid , chemistry , sodium channel , stereochemistry , sodium , pharmacology , medicine , organic chemistry
The lupin alkaloid sparteine is a well‐known chiral diamine with a range of applications in asymmetric synthesis, as well as a blocker of voltage‐gated sodium channels (VGSCs). However, there is only scarce information on the VGSC‐blocking activity of sparteine derivatives where the structure of the parent alkaloid is retained. Building on the recent renewed availability of sparteine and derivatives we report herein how modification of sparteine at position 2 produces irreversible blockers of VGSCs. These compounds could be clinically envisaged as long‐lasting local anesthetics.