Structural Study of Pinacidil, a Potassium‐Channel Opener Belonging to the chemical class of  N ‐alkyl‐ N ″‐cyano‐ N ′‐pyridylguanidines | Zendy

Pirotte Bernard | Zendy; de Tullio Pascal | Zendy; Masereel Bernard | Zendy; Schynts Marc | Zendy; Delarge Jacques | Zendy; Dupont Léon | Zendy

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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.

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