3371-56-0Relevant academic research and scientific papers
Synthesis of 2-fluoro-11-hydroxy-N-propylnoraporphine: A potential dopamine D2 agonist
Zhang, Ao,Csutoras, Csaba,Zong, Rushi,Neumeyer, John L.
, p. 3239 - 3242 (2007/10/03)
(Chemical Equation Presented) 2-Fluoro-11-hydroxy-N-propylnoraporphine 4 (2-F-11 -OH-NPa) was synthesized from thebaine in 13 steps with an overall yield of 1.35%. The key steps included the Pd-catalyzed 3-dehydroxylation of 14-hydroxymorphine, SN2 substitution of Ts- by F -, and CH3SO2OH-promoted rearrangement of the substituted morphinandiene. The dopamine binding affinity of this compound was also investigated on rat brain membranes, and as expected, this compound displayed high affinity and selectivity at the D2 receptor.
Transformations of morphine, codeine and their analogues by Bacillus sp
Madyastha,Reddy,Sridhar
, p. 749 - 753 (2007/10/03)
A bacterial strain belonging to the genus Bacillus islolated by enrichment culture technique using morphine as a sole source of carbon transforms morphine and codeine into 14-hydroxymorphinone and 14-hydroxycodeinone as major and 14-hydroxymorphine and 14-hydroxycodeine as minor metabolites, respectively. When the N-methyl group in morphine and codeine are replaced by higher alkyl groups, the organism still retains its ability to carry out 14-hydroxylation as well as oxidation of the C6-hydroxyl group in these N-variants, although the level of metabolites formed are considerably low. The organism readily transforms dihydromorphine and dihydrocodeine into only dihydromorphinone and dihydrocodeinone, respectively, suggesting that the 7,8-double bond is a necessary structural feature to carry out 14-hydroxylation reaction. The cell free extract (20,000 × g supernatant), prepared from morphine grown cells, transforms morphine into 14-hydroxymorphinone in the presence of NAD+, but fails to show activity against testosterone. However, the cell free extract prepared from testosterone grown cells contains significant levels of 17β- hydroxysteroid dehydrogenase but shows no activity against morphine.
