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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylcholine / metabolism
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Acetylcholine / pharmacology
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Amides / chemistry
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Animals
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Area Under Curve
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Benzenesulfonates / chemistry
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Catalysis
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Chemistry, Pharmaceutical / methods*
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Cholinergic Agonists* / chemical synthesis
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Cholinergic Agonists* / pharmacology
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Cyclization
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Guinea Pigs
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Magnetic Resonance Spectroscopy
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Male
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Muscle Contraction / drug effects*
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Muscle Contraction / physiology
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Muscle, Smooth / drug effects*
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Muscle, Smooth / physiology
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Organ Culture Techniques
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Organometallic Compounds* / chemical synthesis
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Organometallic Compounds* / pharmacology
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Receptors, Cholinergic / metabolism*
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Structure-Activity Relationship
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Tetrahydroisoquinolines* / chemical synthesis
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Tetrahydroisoquinolines* / pharmacology
Substances
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Amides
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Benzenesulfonates
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Cholinergic Agonists
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Organometallic Compounds
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Receptors, Cholinergic
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Tetrahydroisoquinolines
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Acetylcholine
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4-toluenesulfonic acid