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Merck

Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators.

Bioorganic & medicinal chemistry (2012-06-29)
Daniella Takács, Ildikó Nagy, Petra Bombicz, Orsolya Egyed, Katalin Jemnitz, Zsuzsanna Riedl, József Molnár, Leonard Amaral, György Hajós
RESUMEN

N-dienylphenothiazines synthesized from tetrazolo[1,5-a]pyridinium salts by treatment with phenothiazine were subjected to catalytic hydrogenation to yield N-butylphenothiazines, whereas transformation of these dienes with borane dimethyl sulfide (BH(3) × Me(2)S) resulted in selective hydroboration of one double bond and full reduction of the other double bond to give 2-hydroxybutylphenothiazines. Position of the hydroxyl group was supported by NMR spectroscopy and verified by X-ray analysis. Comparison of MDR modulatory activity of the new derivatives revealed that the hydroxybutyl compounds are promising candidates for development of novel MDR inhibitors.

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Sigma-Aldrich
Phenothiazine, ≥98%
Sigma-Aldrich
Phenothiazine, purum, ≥98.0% (GC)