Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators

Daniella Takács, Ildikó Nagy, Petra Bombicz, Orsolya Egyed, Katalin Jemnitz, Zsuzsanna Riedl, József Molnár, Leonard Amaral, György Hajós

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4 Citations (Scopus)

Abstract

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 (BH3 × Me2S) 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.

Original languageEnglish
Pages (from-to)4258-4270
Number of pages13
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number14
DOIs
Publication statusPublished - Jul 15 2012

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Keywords

  • Catalytic hydrogenation
  • Dieneamine
  • Hydroboration
  • Multidrug resistance
  • P-gp inhibition

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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