Synthesis and characterization of thiazolo- and thiazinomorphinans and their intermediate products as novel opioid-active derivatives

Attila Sipos, Valeria Follia, Sándor Berényi, S. Antus, Helmut Schmidhammer, Mariana Spetea

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A new procedure was elaborated for the synthesis of potentially opioid-active thiazolo- and thiazinomorphinans. These derivatives and some intermediates related with the synthesis were tested in opioid receptor binding studies. Two compounds showed remarkable μ opioid activities and specificities. The ligand-stimulated [35S]GTPγS assays confirmed for both compounds the potent full agonist profile at the μ receptor and for the benzothiazinomorphinan derivative also the μ receptor full agonist character. The structures of these remarkably effective compounds were analyzed with the aid of computational chemistry calculations.

Original languageEnglish
Pages (from-to)852-858
Number of pages7
JournalArchiv der Pharmazie
Volume345
Issue number11
DOIs
Publication statusPublished - Nov 2012

Fingerprint

Opioid Analgesics
Opioid Receptors
Ligands

Keywords

  • Heterocycles
  • Morphinans
  • Morphine
  • Opioid activity
  • Thiazine
  • Thiazole

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis and characterization of thiazolo- and thiazinomorphinans and their intermediate products as novel opioid-active derivatives. / Sipos, Attila; Follia, Valeria; Berényi, Sándor; Antus, S.; Schmidhammer, Helmut; Spetea, Mariana.

In: Archiv der Pharmazie, Vol. 345, No. 11, 11.2012, p. 852-858.

Research output: Contribution to journalArticle

Sipos, Attila ; Follia, Valeria ; Berényi, Sándor ; Antus, S. ; Schmidhammer, Helmut ; Spetea, Mariana. / Synthesis and characterization of thiazolo- and thiazinomorphinans and their intermediate products as novel opioid-active derivatives. In: Archiv der Pharmazie. 2012 ; Vol. 345, No. 11. pp. 852-858.
@article{9d2446d1d5d14eb6ad860a147cfa245f,
title = "Synthesis and characterization of thiazolo- and thiazinomorphinans and their intermediate products as novel opioid-active derivatives",
abstract = "A new procedure was elaborated for the synthesis of potentially opioid-active thiazolo- and thiazinomorphinans. These derivatives and some intermediates related with the synthesis were tested in opioid receptor binding studies. Two compounds showed remarkable μ opioid activities and specificities. The ligand-stimulated [35S]GTPγS assays confirmed for both compounds the potent full agonist profile at the μ receptor and for the benzothiazinomorphinan derivative also the μ receptor full agonist character. The structures of these remarkably effective compounds were analyzed with the aid of computational chemistry calculations.",
keywords = "Heterocycles, Morphinans, Morphine, Opioid activity, Thiazine, Thiazole",
author = "Attila Sipos and Valeria Follia and S{\'a}ndor Ber{\'e}nyi and S. Antus and Helmut Schmidhammer and Mariana Spetea",
year = "2012",
month = "11",
doi = "10.1002/ardp.201200176",
language = "English",
volume = "345",
pages = "852--858",
journal = "Archiv der Pharmazie",
issn = "0365-6233",
publisher = "Wiley-VCH Verlag",
number = "11",

}

TY - JOUR

T1 - Synthesis and characterization of thiazolo- and thiazinomorphinans and their intermediate products as novel opioid-active derivatives

AU - Sipos, Attila

AU - Follia, Valeria

AU - Berényi, Sándor

AU - Antus, S.

AU - Schmidhammer, Helmut

AU - Spetea, Mariana

PY - 2012/11

Y1 - 2012/11

N2 - A new procedure was elaborated for the synthesis of potentially opioid-active thiazolo- and thiazinomorphinans. These derivatives and some intermediates related with the synthesis were tested in opioid receptor binding studies. Two compounds showed remarkable μ opioid activities and specificities. The ligand-stimulated [35S]GTPγS assays confirmed for both compounds the potent full agonist profile at the μ receptor and for the benzothiazinomorphinan derivative also the μ receptor full agonist character. The structures of these remarkably effective compounds were analyzed with the aid of computational chemistry calculations.

AB - A new procedure was elaborated for the synthesis of potentially opioid-active thiazolo- and thiazinomorphinans. These derivatives and some intermediates related with the synthesis were tested in opioid receptor binding studies. Two compounds showed remarkable μ opioid activities and specificities. The ligand-stimulated [35S]GTPγS assays confirmed for both compounds the potent full agonist profile at the μ receptor and for the benzothiazinomorphinan derivative also the μ receptor full agonist character. The structures of these remarkably effective compounds were analyzed with the aid of computational chemistry calculations.

KW - Heterocycles

KW - Morphinans

KW - Morphine

KW - Opioid activity

KW - Thiazine

KW - Thiazole

UR - http://www.scopus.com/inward/record.url?scp=84868582307&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84868582307&partnerID=8YFLogxK

U2 - 10.1002/ardp.201200176

DO - 10.1002/ardp.201200176

M3 - Article

C2 - 22886624

AN - SCOPUS:84868582307

VL - 345

SP - 852

EP - 858

JO - Archiv der Pharmazie

JF - Archiv der Pharmazie

SN - 0365-6233

IS - 11

ER -