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Synthesis, Physicochemical and Anticonvulsant Properties of New N ‐4‐Arylpiperazin‐1‐yl Amides of (2‐Aza‐1,3‐dioxospiro[4.4]non‐2‐yl)‐ and [4.5]dec‐2‐yl)‐propionic Acid
Author(s) -
Obniska Jolanta,
Kaminski Krzysztof,
Hondo Lukasz,
Zejc Alfred
Publication year - 2007
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200700038
Subject(s) - chemistry , anticonvulsant , reagent , seizure threshold , acetic acid , stereochemistry , medicinal chemistry , epilepsy , organic chemistry , medicine , psychiatry
In continuation of the search of new anticonvulsants, a series of N ‐4‐arylpiperazin‐1‐yl 2‐aza‐1,3‐dioxospiro[4.4]non‐2‐yl‐ ( 5 – 8 ) and [4.5]dec‐2‐yl‐ ( 9 – 15 ) propionamides, structurally related to the previously described N ‐4‐arylpiperazin‐1‐yl amides of 2‐aza‐1,3‐dioxospiro[4.5]dec‐2‐yl‐acetic acid, were synthesized. The designed compounds 5 – 15 were prepared by condensation of the formerly obtained (2‐aza‐1,3‐dioxospiro[4.5]dec‐2‐yl)‐ ( 3 ) and (2‐aza‐1,3‐dioxo[4.4]non‐2‐yl)‐( 4 ) propionic acids with the appropriately substituted 4‐arylpiperazines, in the presence of the N,N ‐carbonyldiimidazole (CDIM) reagent. All the compounds were tested for their anticonvulsant activity in the maximum electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure threshold tests. Several compounds 7–10 , 13 and 14 revealed protection in the MES screening.