New octahydroquinazoline derivatives: synthesis and hypotensive activity.
Several novel 1-(4-chlorophenyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydro-5-oxo-3-(substitutedphenyl)quinazoline derivatives (2-21) structurally similar to prazosin, were prepared using Mannich reaction of 3-(4-chlorophenylamino)-5,5-dimethyl-2-cyclohexenone (1) with different aromatic amines in the presence of formaline. The structures of the quinazoline derivatives were established using elemental and spectral analyses. Compounds 18, 20 and 21 were found to possess a high hypotensive effect through their expected α(1)-blocking activity like the clinically used drug prazosin but with advantageous of being did not cause reflex tachycardia and having prolonged duration of action when tested in adrenaline-induced hypertension in anaesthetized rats.
el-Sabbagh
O I
OI
Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt. osamaelsabbagh@yahoo.com
Shabaan
Mohamed A
MA
Kadry
Hanan H
HH
Al-Din
Ehab Saad
ES
D000818:Animals; D000959:Antihypertensive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013055:Spectrophotometry, Infrared
D000959:Antihypertensive Agents; D011799:Quinazolines