Bodensteiner, Julian and Baumeister, Paul and Geyer, Roland and Buschauer, Armin and Reiser, Oliver (2013) Synthesis and pharmacological characterization of new tetrahydrofuran based compounds as conformationally constrained histamine receptor ligands. ORGANIC & BIOMOLECULAR CHEMISTRY, 11 (24). pp. 4040-4055. ISSN 1477-0520,
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A series of tetrahydrofuran based compounds with a bicyclic core that provides conformational restriction were synthesized and investigated by radioligand displacement studies and functional [S-35]GTP gamma S binding assays at the human histamine receptor (hHR) subtypes. The amines 8a and 8b ((1S,3R,5S,6R)- and ((1S,3S,5S,6R)-3-(1H-imidazol-5-yl)-2-oxabicyclo[3.1.0]hexan-6-yl)methanamine), exhibited submicromolar K-i values at the hH(3)R with 10-fold higher affinities than their corresponding (6S)-epimers and 25- and >34-fold selectivity over the hH(4)R, respectively. Both compounds act as neutral antagonists at the hH(3)R with K-B values of 181 and 32 nM, respectively. The cyanoguanidines of the imidazole series and the oxazole analogues turned out to be inactive at all hHR subtypes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PRESYNAPTIC H-3 RECEPTORS; RAT-BRAIN CORTEX; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); SULFONYLMETHYL ISOCYANIDES; CONSTITUTIVE ACTIVITY; H-4-RECEPTOR AGONIST; STIMULATED BINDING; MOLECULAR-CLONING; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Apr 2020 07:15 |
| Last Modified: | 29 Apr 2020 07:15 |
| URI: | https://pred.uni-regensburg.de/id/eprint/17413 |
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