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Synthesis and anticonvulsant activity of 3 H ‐imidazo[4,5‐ c ]‐pyridazine, 1 H ‐imidazo[4,5‐ d ]pyridazine and 1 H ‐benzimidazole analogues of 9‐(2‐fluorobenzyl)‐6‐methylamino‐9 H ‐purine
Author(s) -
Kelley James L.,
Thompson James B.,
Styles Virgil L.,
Soroko Francis E.,
Cooper Barrett R.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320503
Subject(s) - pyridazine , chemistry , anticonvulsant , benzimidazole , stereochemistry , imidazole , bicyclic molecule , pyrimidine , medicinal chemistry , organic chemistry , epilepsy , neuroscience , biology
The 3 H ‐imidazo[4,5‐ c ]pyridazine, 1 H ‐imidazo[4,5‐ d ]pyridazine, and 1 H ‐benzimidazole analogues of the potent anticonvulsant purine 9‐(2‐fluorobenzyl)‐6‐methylamino‐9 H ‐purine (1, 78U79) were synthesized and tested for anticonvulsant activity. The 3 H ‐imidazo[4,5‐ c ]pyridazines 8 and 9 were prepared in five stages from 3,4,5‐trichloropyridazine (2) . The 1 H ‐imidazolo[4,5‐ d ]pyridazine 15 was synthesized in four stages from 5‐[(benzyloxy)methyl]‐1,5‐dihydro‐4 H ‐imidazo[4,5‐ d ] pyridazin‐4‐one (10a) . The benz‐imidazole analogues 18 and 20 were prepared from 2,6‐dinitroaniline in three stages. These compounds were one‐tenth or less as active as 1 in protecting rats against maximal electroshock‐induced seizures.