title: Synthesis and bronchodilatory activity of some nitrogen bridgehead compounds.
abstract: A series of tricyclic nitrogen bridgehead compounds 7-22 have been synthesised and evaluated for their in vitro bronchodilatory activity using isolated guinea pig tracheal chain, precontracted with acetylcholine. The relaxant effect of 2,3,4,5-tetrahydroazepino[2,1-b]-8,9-dimethoxyquinazolin-11(1H)-one (7) (DPJ-386) was greater than that of theophylline, aminophylline and quinazoline derivative 3, which lacks methoxy groups at positions 8 and 9. Various nitrogen containing functionalities such as benzylamino, acetamido, benzamido and phthalimido were also introduced at 9 position of 3. This resulted in loss of relaxation activity in precontracted guinea pig tracheal chain. These results show that the better relaxation property possessed by compound 7 hydrochloride is due to methoxy groups at 8 and 9 positions.
authors: University Institute of Pharmaceutical Sciences (formerly Department of Pharmaceutical Sciences), Panjab University, Chandigarh 160 014, India. dharampjindal@yahoo.co.in
authors: Dharam Paul
authors: DP
authors: Jindal
authors: Ravinder Singh
authors: RS
authors: Bhatti
authors: Seema
authors: S
authors: Ahlawat
authors: Ranju
authors: R
authors: Gupta
mesh_terms: D000109:Acetylcholine; D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001993:Bronchodilator Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006168:Guinea Pigs; D066298:In Vitro Techniques; D009126:Muscle Relaxation / Q000187:drug effects*; D009130:Muscle, Smooth / Q000187:drug effects; D009584:Nitrogen / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D014132:Trachea / Q000187:drug effects*
chemical_list: C470127:2,3,4,5-tetrahydroazepino(2,1-b)-8,9-dimethoxyquinazolin-11(1H)-one; D001952:Bridged-Ring Compounds; D001993:Bronchodilator Agents; D011799:Quinazolines; D009584:Nitrogen; D000109:Acetylcholine