Synthesis, structural analysis and pharmacological effects of N2-substituted 3,4-dihydrobenzo[h]quinolin-2-amines.
The introduction outlines possibilities for the design of potentially pharmacologically interesting new modifications of phenylethylamine (1) and reviews already known and nearly prepared derivatives of 1 with bridged side chains. The N2-substituted 3,4-dihydrobenzo[h]quinolin-2-amines 11a-e represent bridged beta-azanaphthylethenamines or naphthyl-formamidines. Their synthesis started from 3-chloro-N-(1-naphthyl)propionamide (14) and led via dihydrobenzoquinolinone 15, thione 19 and methylthiobenzoquinoline hydroiodide 20. HI as intermediates first to the hydroiodides of 11a-e. Treatment of 11c, d. HI with sodium hydroxide yielded the free amines 11c, d. Structure, tautomerism, (Z, E)-isomerism and conformation of the prepared benzoquinolines were studied and elucidated by one and two dimensional NMR. A synopsis of the manyfold pharmacological effects, which were found in the course of the testing of 11a-e. HI, completes the paper.
Wendelin
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W
Institute of Pharmaceutical Chemistry, Karl-Franzens-University Graz, Austria.
Keimelmayr
H
H
Gössnitzer
E
E
Abou el Ella
D
D
D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002317:Cardiovascular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002415:Cats; D002491:Central Nervous System Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015195:Drug Design; D006168:Guinea Pigs; D006439:Hemodynamics / Q000187:drug effects; D066298:In Vitro Techniques; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D051381:Rats
D000634:Aminoquinolines; D002317:Cardiovascular Agents; D002491:Central Nervous System Agents