2-benzazepines. 5. Synthesis of pyrimido[5,4-d][2]benzazepines and their evaluation as anxiolytic agents.
A series of 5H-pyrimido[5,4-d][2]benzazepines has been synthesized, starting from the corresponding 2-benzazepin-5-ones, and evaluated as potential anxiolytic agents. Selected compounds from this series show a pharmacological profile of action different than that of diazepam. They are more potent than diazepam in the anti-pentylenetetrazole test and in the [3H]diazepam binding assay, yet show less activity in the inclined screen test. A pharmacological data profile is given for 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d] [2]benzazepine (7c). The structure-activity relationships of these potential anxiolytic agents are discussed.
D000818:Animals; D014151:Anti-Anxiety Agents / Q000138:chemical synthesis*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000494:pharmacology; D001681:Biological Assay; D003975:Diazepam / Q000378:metabolism; D004353:Drug Evaluation, Preclinical; D004347:Drug Interactions; D000431:Ethanol / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D011743:Pyrimidines / Q000138:chemical synthesis / Q000494:pharmacology; D011956:Receptors, Cell Surface / Q000187:drug effects / Q000378:metabolism; D011963:Receptors, GABA-A; D012018:Reflex / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D014151:Anti-Anxiety Agents; D001552:Benzazepines; D007202:Indicators and Reagents; D011743:Pyrimidines; D011956:Receptors, Cell Surface; D011963:Receptors, GABA-A; D000431:Ethanol; D003975:Diazepam