306994-53-6

Upstream product

• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 74-89-5 methylamine 

Downstream Products

• 1046786-21-3 (1R,2R,4S,5S)-3-methyl-7-((S)-1-naphthalen-1-ylethyl)-2,4-bis(4-nitrophenyl)-9-oxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester 
• 1046786-19-9 (1R,2R,4S,5S)-3-methyl-2,4-bis(4-nitrophenyl)-9-oxo-7-((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Synthesis and opioid receptor affinity of a series of 2,4-diaryl-substituted 3,7-diazabicylononanones

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.

Conformational and configurational behaviour of κ-agonistic 3,7-diazabicyclo[3.3.1]nonan-9-ones - Synthesis, nuclear magnetic resonance studies and semiempirical PM3 calculations

2,4-Diaryl substituted 3,7-diazabicyclo[3.3.1]nonan-9-one 1,5-diesters were found to have a high affinity for κ-opioid receptors. To develop highly potent analgesics, the purpose of this study was the synthesis and the structural characterisation of the novel 2,4-bis(4-nitrophenyl), 2,4-bis(3-nitrophenyl), 2,4-bis(4-quinolyl), 2,4-bis(2-quinolyl), 2,4-bis(1-naphthyl) and 2,4-bis(2-naphthyl) substituted 3,7-diazabicyclo[3.3.1]nonan-9-one 1,5-diesters by means of NMR spectroscopy and molecular modelling. It could be proved that several derivatives undergo trans-cis-isomerisation of the aromatic rings linked to the rigid skeleton whereas others show rotational isomerisation. Semiempirical quantum-chemical PM3 calculations were performed to analyse the thermodynamic stability of the isomers as well as the mechanism of the trans-cis-or cis-trans-conversion.