89232-80-4Relevant academic research and scientific papers
Synthesis and characterization of N-demethylated metabolites of malachite green and leucomalachite green
Cho, Bongsup P.,Yang, Tianle,Blankenship, Lonnie R.,Moody, Joanna D.,Churchwell, Mona,Beland, Frederick A.,Culp, Sandra J.
, p. 285 - 294 (2007/10/03)
Malachite green (MG), a triphenylmethane dye used to treat fungal and protozoan infections in fish, undergoes sequential oxidation to produce various N-demethylated derivatives (monodes-, dides(sym)-, dides(unsym)-, trides-, and tetrades-) both before and after reduction to leucomalachite green (LMG). The close structure resemblance of the metabolites with aromatic amine carcinogens implicates a potential genotoxicity from exposure to MG. The availability of the synthetic standards is important for metabolic and DNA adduct studies of MG. This paper describes a simple and versatile method for the synthesis of MG, LMG, and their N-demethylated metabolites. The synthesis involves a coupling of 4-(dimethylamino)-benzophenone or 4-nitrobenzophenone with the aryllithium reagents derived from appropriately substituted 4-bromoaniline derivatives, followed by treatment with HCl in methanol. The resulting cationic MG and their leuco analogues showed systematic UV/vis spectral and tandem mass fragmentation patterns consistent with sequential N-demethylation. The extensive 1H and 13C spectral assignments of the metabolites were aided by the availability of 13C7-labeled MG and LMG. The results indicate the existence of a resonance structure with the cationic charge located in the central methane carbon (C7). The synthetic procedure is general in scope so that it can be extended to the preparation of N-demethylated metabolites of other structurally related N-methylated triphenylmethane dyes.
Synthesis of N-desmethyl derivatives of 17α-acetoxy-11β(4-N,N- dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione and mifepristone: Substrates for the synthesis of radioligands
Rao, Pemmaraju N.,Acosta, C. Kirk,Cessac, James W.,Bahr, Martin L.,Kim, Hyun K.
, p. 205 - 212 (2007/10/03)
The syntheses of N-desmethyl derivatives of CDB-2914 and the mono-N- desmethyl derivative of Mifepristone are described. We also describe the use of the mono-desmethyl derivatives as substrates for the synthesis of N- tritomethyl derivatives of CDB-2914 a
11β-arylestradienes, their production, and pharmaceutical preparations containing same
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, (2008/06/13)
11β-Arylestradienes of general Formula I are disclosed STR1 wherein R2 is a hydrogen atom, a methyl group, or an ethyl group, R3 is a hydrogen atom or an acyl group, R1 and A-B have various meanings, which possess antigest
