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Structural Study of Pinacidil, a Potassium‐Channel Opener Belonging to the chemical class of N ‐alkyl‐ N ″‐cyano‐ N ′‐pyridylguanidines
Author(s) -
Pirotte Bernard,
de Tullio Pascal,
Masereel Bernard,
Schynts Marc,
Delarge Jacques,
Dupont Léon
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760318
Subject(s) - chemistry , pinacidil , potassium channel opener , tautomer , potassium channel , potassium , crystal structure , solid state , stereochemistry , alkyl , crystallography , organic chemistry , biophysics , medicine , glibenclamide , biology , diabetes mellitus , endocrinology
The crystal structure of the potassium‐channel opener ( R , S )‐pinacidil ( 2 ) was determined by X‐ray crystallography. Its N ′, N ″‐disubstitued N ‐cyanoguanidine fragment was found to exhibit an unusual (Z,Z)‐conformation. X‐Ray and NMR data obtained with 2 are consistent with the predominance of the 4‐aminopyridine species over an iminopyridine tautomer in the solid state and in solution. These new structural informations may help further comparative studies of 2 and other potassium‐channel openers in elucidating structure‐activity relationships.