124189-54-4Relevant academic research and scientific papers
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
Siener, Tom,Holzgrabe, Ulrike,Drosihn, Susanne,Brandt, Wolfgang
, p. 1827 - 1834 (1999)
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.
