Synthesis and pharmacological evaluation of thiazole and isothiazole derived apomorphines

Attila Sipos, Franziska K.U. Mueller, Jochen Lehmann, Sándor Berényi, Sándor Antus

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11 Citations (Scopus)


We have presented the synthesis of novel thiazolo- and isothiazolo- apomorphines 12-17 resulting - in part - from an unexpected isomerization step occurred during the acid-catalyzed rearrangement of precursor thiazolo-morphinandienes 3-5. These 2,3-disubstituted apomorphines represent a new group of A-ring substituted aporphines. The receptor binding studies revealed that with the exception of two derivatives all the tested compounds have limited affinity for dopamine-receptor subtypes. Functional calcium assay for the most active isothiazolo-apomorphine showed higher affinities for D 1 and D2L subtypes. The docking of these ligands has been modelled to human D2 and D3 receptors. On the basis of the predicted models, we identified an important cation-p interaction for the binding of isothiazolo-apomorphine 16.

Original languageEnglish
Pages (from-to)557-568
Number of pages12
JournalArchiv der Pharmazie
Issue number10
Publication statusPublished - Oct 1 2009



  • Benzothiazole-benzisothiazole isomerization
  • Docking models
  • Dopamine receptor activity
  • Thiazole moiety

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery

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