title: Synthesis and contractile activity of substituted 1,2,3,4-tetrahydroisoquinolines.
abstract: A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydro-isoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of ketoamides with organomagnesium compounds, followed by cyclization in the presence of catalytic amounts of p-toluenesulfonic acid (PTSA). A number of substituents at the C-1 in the isoquinoline skeleton were introduced varying either carboxylic acid or organomagnesium compound. Some of the obtained 1,1-dialkyl-1,2,3,4-tetrahydro-isoquinolines possess contractile activity against guinea pig's gastric smooth muscle preparations.
authors.affiliation: Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen Street, 4000 Plovdiv, Bulgaria. ivanov@uni-plovdiv.bg
authors.forename: Iliyan
authors.initials: I
authors.lastname: Ivanov
authors.forename: Stoyanka
authors.initials: S
authors.lastname: Nikolova
authors.forename: Dimo
authors.initials: D
authors.lastname: Aladjov
authors.forename: Iliyana
authors.initials: I
authors.lastname: Stefanova
authors.forename: Plamen
authors.initials: P
authors.lastname: Zagorchev
mesh_terms: D000109:Acetylcholine / Q000378:metabolism / Q000494:pharmacology; D000577:Amides / Q000737:chemistry; D000818:Animals; D019540:Area Under Curve; D001557:Benzenesulfonates / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D018679:Cholinergic Agonists / Q000138:chemical synthesis / Q000494:pharmacology; D003500:Cyclization; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009119:Muscle Contraction / Q000187:drug effects* / Q000502:physiology; D009130:Muscle, Smooth / Q000187:drug effects* / Q000502:physiology; D009924:Organ Culture Techniques; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D011950:Receptors, Cholinergic / Q000378:metabolism*; D013329:Structure-Activity Relationship; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000577:Amides; D001557:Benzenesulfonates; D018679:Cholinergic Agonists; D009942:Organometallic Compounds; D011950:Receptors, Cholinergic; D044005:Tetrahydroisoquinolines; D000109:Acetylcholine; C029501:4-toluenesulfonic acid