Pharmaceutical Chemistry Journal

, Volume 51, Issue 7, pp 540–545 | Cite as

Chiral Analogs of a-tocopherol. Antioxidant Activity of the (R) and (S) Enantiomers of {2-[6-hydroxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}-trimethylammonium-p-toluenesulfonate Depending on Their Configuration

  • G. D. Gamalevich
  • A. L. Vlasyuk
  • É. P. Serebryakov
Article
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Starting with the (R) and (S) enantiomers of 2-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethanol, prepared previously by partial acylation of the corresponding racemic alcohol in the presence of the most easily available lipase, from the yeast Candida cylindracea, a four-stage syntheses was developed for both enantiomers of {2-[6-hydroxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}trimethylammonium p-toluenesulfonate (MDL-73404), which are chiral analogs of α-tocopherol. Comparative biomedical testing of samples of MDL-73404 salts with different enantiomer compositions in relation to their effects on the generation of reactive oxygen species by peritoneal macrophages from white rats in systems containing luminol or lucigenin demonstrated different levels of inhibition of spontaneous and 12-O-myristyl-13-O-acetylphorbol-activated macrophage chemiluminescence.

Keywords

2-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethanol yeast Candida cylindracea lipase enantiomeric acetylation {2-[6-hydroxy-2,5,7,8-tetramethylchroman-2-yl]ethyl}trimethylammonium p-toluenesulfonate (MDL-73404) (R) and (S) enantiomers antioxidant activity spontaneous and 12-O-myristyl-13-O-acetylphorbol-activated chemiluminescence 

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • G. D. Gamalevich
    • 1
  • A. L. Vlasyuk
    • 1
  • É. P. Serebryakov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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