synthesis and contractile activity of substituted 1,2,3,4-tetrahydroisoquinolines合成和收缩活动取代的1、2、3 4-tetrahydroisoquinolines.pdf
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Molecules 2011, 16, 7019-7042; doi:10.3390/molecule
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molecules
ISSN 1420-3049
/journal/molecules
Article
Synthesis and Contractile Activity of Substituted
1,2,3,4-Tetrahydroisoquinolines
Iliyan Ivanov 1,*, Stoyanka Nikolova 1, Dimo Aladjov 1, Iliyana Stefanova 2 and
Plamen Zagorchev 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; E-Mails: ivanov@uni-plovdiv.bg (I.I.);
plamenz@gbg.bg (P.Z.); Tel.: +359-32-261-349; Fax: +359-32-261-403.
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
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