145160-29-8Relevant academic research and scientific papers
Synthesis and opioid receptor affinity of a series of 2,4-diaryl-substituted 3,7-diazabicylononanones
Siener,Cambareri,Kuhl,Englberger,Haurand,Kogel,Holzgrabe
, p. 3746 - 3751 (2007/10/03)
3,7-Diazabicyclo[3.3.1]nonan-9-ones having aryl rings in positions 2 and 4 with systematically varied substituents were synthesized using a double Mannich procedure. Radioligand binding assays were performed to measure the affinity of the compounds to the μ-, δ-, and κ-opioid receptors. The affinity of all 2,4-diphenyl-substituted 3,7-diazabicyclo[3.3.1]nonan-9-ones to the μ- and δ-receptors was found to be low. In contrast, with exception of the nitro- and cyanophenyl-substituted compounds, most of the diazabicycles showed considerable affinity for the κ-receptor. In particular, the m-fluoro-, p-methoxy-, and m-hydroxy-substituted compounds have an affinity in the submicromolar range. Due to solubility problems in aqueous media, salts of HZ2 were synthesized. The methiodide shows high κ-affinity and may, thus, be a promising candidate for development of a peripheral κ-agonist, e.g. for use in the case of rheumatoid arthritis.
Synthesis and stereochemistry of potential opioid-like 2,4-m-diarylsubstituted 3,7-diazabicyclo[3.3.1]nonan-9-one-1,5-diesters
Holzgrabe,Erciyas
, p. 657 - 663 (2007/10/02)
The 2,4-di-2-pyridyl-substituted 7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one-1,5-diester shows a reasonable κ-agonistic activity in the mouse vas deferens test. - To enhance the analgetic activity derivatives with m-Cl-, m-CH3-, m-OCH3/su
