Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators

Daniella Takács, Ildikó Nagy, P. Bombicz, O. Egyed, K. Jemnitz, Z. Riedl, J. Molnár, Leonard Amaral, G. Hajós

Research output: Contribution to journalArticle

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

Fingerprint

Boranes
Hydrogenation
X ray analysis
Hydroxyl Radical
Modulators
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Salts
X-Rays
Derivatives
phenothiazine
dimethyl sulfide

Keywords

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

ASJC Scopus subject areas

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

Cite this

Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators. / Takács, Daniella; Nagy, Ildikó; Bombicz, P.; Egyed, O.; Jemnitz, K.; Riedl, Z.; Molnár, J.; Amaral, Leonard; Hajós, G.

In: Bioorganic and Medicinal Chemistry, Vol. 20, No. 14, 15.07.2012, p. 4258-4270.

Research output: Contribution to journalArticle

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AU - Jemnitz, K.

AU - Riedl, Z.

AU - Molnár, J.

AU - Amaral, Leonard

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