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Laboratory of Pharmaceutical Education (Chemistry), MOHRI

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Kunihiko Mohri, Ph.D.Professor

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Facile synthesis of heterocyclic compounds and biological activity of new synthesizedheterocycles.

  1. Facile Synthesis of substituted 1,2,3,4-tetrahydroisoquinolines and their analoguesusing modified Pictet-Spengler reaction.
  2. Biological activities of new synthesized 1-substituted 1,2,3,4-tetrahydro-isoquinolines.

Outline of our study

1-Substituted tetrahydroisoquinolines (TIQs) are well known to be a compound which isclosely related to Parkinson’s disease. Pictet-Spengler reaction is one of the famousmethods of the synthesis of TIQs, although the reaction has limitation based on thereactivity and the stability of imine-intermediate of the reaction that is produced by thecondensation of starting materials such as arylethylamines and carbonyl compounds. Wehave already developed new method, which allows synthesis of TIQs and their analoguesmore efficient under the mild reaction condition, by improving the Pictet-Spenglerreaction. This method leads to the cyclization under the mild acidic reaction condition dueto the promoted electrophilicity of the intermediate acyliminium ion by the acylation of theimine. This method has another advantage that any purification of the unstableintermediate is not done, since the reaction is performed as an one-pot system.Moreover, the application of the method can be expanded to the synthesis oftetrahydrobenzooxazepines, benzotiazepines and tricyclic heterocompound such astetrahydrobenzothieno[3,2-c]pyridine, tetrahydrobenzo-thieno[2,3-c]pyridine. The optimizations of the reaction conditions are proceeding now. Onthe other hands, the biological activities of TIQs which are synthesized by our method areevaluating compared with other compounds related to Parkinson’s disease.

Laboratory

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Showa Pharmaceutical University

3-3165 Higashi-Tamagawagakuen,
Machidashi,Tokyo 194-8543, Japan
TEL +81-42-721-1511

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