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. 2011 Aug 16;16(8):7019-42.
doi: 10.3390/molecules16087019.

Synthesis and contractile activity of substituted 1,2,3,4-tetrahydroisoquinolines

Iliyan Ivanov  1 , Stoyanka Nikolova, Dimo Aladjov, Iliyana Stefanova, Plamen Zagorchev
Affiliations

Synthesis and contractile activity of substituted 1,2,3,4-tetrahydroisoquinolines

Iliyan Ivanov et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Retrosynthetic scheme for the synthesis of both 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines.
Scheme 2
Scheme 2
Synthesis of starting ketoamides.
Scheme 3
Scheme 3
Synthesis of 1-substituted and 1,1-disubstituted-1,2,3,4-tetrahydroisoquinolines.
Scheme 4
Scheme 4
Formation of styrenes 8.
Figure 1
Figure 1
Change of spontaneous contractile activity of gastric smooth muscles preparation after using 1-substituted 1,2,3,4-tetrahydroisoquinoline derivatives and papaverine, normal activity is taken for 100%.
Figure 2
Figure 2
Change of spontaneous contractile activity of gastric smooth muscles preparation after using 1,1-disubstituted 1,2,3,4-tetrahydroisoquinoline derivatives and papaverine, normal activity is taken for 100%.
Figure 3
Figure 3
Change of spontaneous contractile activity of gastric smooth muscles preparation after using styrenes and papaverine, normal activity is taken for 100%.
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