Synthesis and evaluation of 1,omega-diaryl-l,omega-alkanediamines related to the fibrinolytic bis(tetrahydroisoquinolines) and bis(benzylamines).
Since the previously investigated bis(tetrahydroisoquinolines) 1 and bis(benzylamines) 2 may be classified as 1,omega-diaryl-1,omega-alkanediamines, it appeared worthwhile to examine this structural concept as a guideline for predicting significant fibrinolytic activity. The prototype bis compounds 7, 14, 15, and 29-31, which were synthesized for this purpose, incorporate such molecular modifications as replacement of the tetrahydroisoquinoline nuclei of series 1 with tetrahydrobenzazepine (7) and tetrahydropyridoindole (14-15) nuclei. The latter compounds, as well as 29-31 which possess features common to both series 1 and 2, showed good to moderate activity in the standard rat (ip) screen. Significant departures from the 1,omega-diaryl-1,omega-alkanediamine structural concept led to compounds (35 and 40) of weak to moderate activity.
D000588:Amines / Q000138:chemical synthesis*; D000818:Animals; D001596:Benzylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D003959:Diamines / Q000138:chemical synthesis* / Q000494:pharmacology; D005342:Fibrinolysis / Q000187:drug effects; D005343:Fibrinolytic Agents / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D000588:Amines; D001596:Benzylamines; D003959:Diamines; D005343:Fibrinolytic Agents; D007546:Isoquinolines