DESIGN AND SYNTHESIS OF NEW POTENTIAL LIGANDS OF µ- AND δ-OPIATE RECEPTORS IN THE SERIES OF DECAHYDRO-4<i>a</i>-HYDROXY-6-ISOQUINOLONE

Authors

  • М. Л. Косточка V. V. Zakusov State Institute of Pharmacology, Russian Academy of Medical Sciences, 125315 Moscow
  • В. Г. Винокуров V. V. Zakusov State Institute of Pharmacology, Russian Academy of Medical Sciences, 125315 Moscow
  • В. П. Лезина V. V. Zakusov State Institute of Pharmacology, Russian Academy of Medical Sciences, 125315 Moscow
  • П. М. Клодт V. V. Zakusov State Institute of Pharmacology, Russian Academy of Medical Sciences, 125315 Moscow

DOI:

https://doi.org/10.1007/6695

Keywords:

4a-hydroxydecahydroisoquinolines, 4a-hydroxy-2, 3, 8a-trimethyl-8-phenyldecahydro-6-isoquinolone, morphine, 1, 2, 5-trimethyl-4-piperidone, agonists, Robinson ring fusion, MVD model, opiate activity

Abstract

A new approach has been proposed for simplification of the morphine molecule in order to obtain new potential  µ- and  δ-opiate receptor ligands. The reaction  of 1,2,5-trimethyl-4-piperidone  and  2,2-dimethyl-4-tetrahydropyrone with substituted benzalacetones under Robinson ring fusion conditions gave decahydroisoquinoline and decahydroisochromene derivatives. A thorough  conformational  analysis  of these products was carried out. The effect of the products on the functional activity of opiate receptors on the mouse vas deferens isolated organ (MVD) model was studied. Prior screening showed that 8-(p-dimethylaminophenyl)-4a-hydroxy-2,3,8a-trimethyldecahydro-6-isoquinolone  displays opiate activity and has agonist properties.

How to Cite
Kostochka, M. L.; Vinokurov, V. G.; Lezina, V. P.; Klodt, P. M. Chem. Heterocycl. Compd. 2009, 45, 715. [Khim. Geterotsikl. Soedin. 2009, 895.]

For this article in the English edition see DOI 10.1007/s10593-009-0324-5


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Published

2022-03-24

Issue

No. 6 (2009)

Section

Original Papers