縮合Pyridazine誘導体の合成研究(第1報)2-Substituted-4,4a, 5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one誘導体, 及び関連化合物の合成とBenzodiazepine受容体親和性

概要

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A series of 2-substituted-4,4a, 5,6-tetrahydrobenzo [h] cinnolin-3 (2H)-ones and related compounds were synthesized and tested for their ability to displace [^3H] diazepam from rat brain membranes. Among them, compounds bearing 4-methoxyphenyl, 4-chloro-phenyl, or 4-methylphenyl group at the position-2 were found to have high affinity to the benzodiazepine receptor. 2-(4-Methoxyphenyl)-9-methyl- and 2-(4-methoxyphenyl)-9-methoxy-4,4a, 5,6-tetrahydrobenzo [h] cinnolin-3 (2H)-ones (8b-14 and 8b-15,respectively) showed a potent affinity comparable to that of diazepam. These results suggest that a topographical planarity or pseudoplanarity of these molecules is essential for high affinity to the benzodiazepine receptor. The structure-activity relationships are discussed.
公益社団法人日本薬学会の論文
1990-08-25