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Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines
Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen Street, 4000 Plovdiv, Bulgaria
Department of Biophysics, Medical University, 15A Vasil Aprilov Street, 4000 Plovdiv, Bulgaria
* Authors to whom correspondence should be addressed.
Received: 22 July 2011; in revised form: 10 August 2011 / Accepted: 11 August 2011 / Published: 16 August 2011
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.
Keywords: Grignard reagent; tetrahydroisoquinolines; contractile activity
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Ivanov, I.; Nikolova, S.; Aladjov, D.; Stefanova, I.; Zagorchev, P. Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines. Molecules 2011, 16, 7019-7042.
Ivanov I, Nikolova S, Aladjov D, Stefanova I, Zagorchev P. Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines. Molecules. 2011; 16(8):7019-7042.
Ivanov, Iliyan; Nikolova, Stoyanka; Aladjov, Dimo; Stefanova, Iliyana; Zagorchev, Plamen. 2011. "Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines." Molecules 16, no. 8: 7019-7042.