Next Article in Journal
Development of a Highly Sensitive and Specific Immunoassay for Determining Chrysoidine, A Banned Dye, in Soybean Milk Film
Next Article in Special Issue
Synthesis and Electrophilic Substitutions of Novel Pyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidines
Previous Article in Journal
Antiviral Properties of Lactoferrin—A Natural Immunity Molecule
Previous Article in Special Issue
Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives
Molecules 2011, 16(8), 7019-7042; doi:10.3390/molecules16087019

Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines

1,* , 1, 1, 2 and 2,*
1 Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen Street, 4000 Plovdiv, Bulgaria 2 Department of Biophysics, Medical University, 15A Vasil Aprilov Street, 4000 Plovdiv, Bulgaria
* Authors to whom correspondence should be addressed.
Received: 22 July 2011 / Revised: 10 August 2011 / Accepted: 11 August 2011 / Published: 16 August 2011
(This article belongs to the Special Issue Heterocycles)
Download PDF [510 KB, uploaded 18 June 2014]


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 Grignard reagent; tetrahydroisoquinolines; contractile activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert