Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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%.
See this image and copyright information in PMC

References

    1. Rodger I.W., Hersom A.S., Waigh R.D. Actions of two dopamine derivatives at adreno- and cholinoceptors. J. Med. Chem. 1979;22:117–119. doi: 10.1021/jm00187a027. - DOI - PubMed
    1. Lundstrom J. In: The Alkaloids. Brossi A., editor. Vol. 21. Academic Press; New York, NY, USA: 1983. p. 255.
    1. Collins M.A. In: The Alkaloids. Brossi A., editor. Vol. 21. Academic Press; New York, NY, USA: 1983. p. 329.
    1. Chrzanowska M., Schönenberg B., Brossi A., Flippen-Anderson J.L. Mammalian alkaloids: Configurations of optically active salsoline- and 3′,4′-Dideoxynorlaudanosoline-1-carboxylic acids. Helv. Chim. Acta. 1987;70:1721–1731. doi: 10.1002/hlca.19870700707. - DOI
    1. Czarnocki Z., Suh D., MacLean D.B., Hultin P.G., Szarek W.A. Enantioselective synthesis of 1-substituted tetrahydroisoquinoline-1-carboxylic acids. Can. J. Chem. 1992;70:1555–1561. doi: 10.1139/v92-191. - DOI

Publication types

MeSH terms

LinkOut - more resources