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

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.

Possible role of 18-kDa translocator protein (TSPO) in etifoxine-induced reduction of direct twitch responses in isolated rat nerve-skeletal muscle preparations

“…The mechanical responses produced by direct stimulation were recorded isometrically with a force transducer (TRI 201, LSi LETICA; Panlab S.L., Barcelona, Spain) and a computerbased system. This allowed the recording, archiving and statistical analysis of mechanical muscle activity as described previously [21]. The interval of discretization was 1 millisecond.…”

Computational and Experimental Study on Molecular Structure of Benzo[g]pyrimido[4,5-b]quinoline Derivatives: Preference of Linear over the Angular Isomer

“…Compared with other derivatives that exhibit high fluorescence, quinolone derivatives are among the best candidates in the design of electroluminescent materials [24,25]. Its fusion with other interesting heterocyclic nucleus such as pyrimidine have afforded systems with high usefulness, such the pyrimido [4,5-b]quinoline, which have been synthesized by diverse procedures, involving condensation and cyclocondensation reactions [26][27][28][29][30][31][32][33][34].…”

One‐Pot α‐Amidosulfone‐Mediated Variation of the Pictet–Spengler Tetrahydroisoquinoline Synthesis, Suitable for Amide‐Type Substrates

“…In conclusion, we have developed a one‐pot Pictet–Spengler protocol that, unlike most previously known methods, allows the efficient preparation of tetrahydroisoquinolines from amide‐type substrates, aldehydes and p ‐toluenesulfinic acid, without the need for strong Lewis or Brønsted acid catalysts 26. The application of this method to the very efficient preparation of a library of pyrazino[2,1‐ b ]isoquinolines, important precursors to anticancer saframycin analogues, was also achieved.…”