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 | Zendy

Kelley James L. | Zendy; Thompson James B. | Zendy; Styles Virgil L. | Zendy; Soroko Francis E. | Zendy; Cooper Barrett R. | Zendy

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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.

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