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Synthesis and antitrypanosomal activity of 2-aminomethyl-1-(2-oxyphenyl)naphthalenes |
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| Authors: | Gerhard Bringmann Robert-Michael Pfeifer Kristina Hartner Reto Brun Eva-Maria Peters |
| Affiliation: | a Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany b Institute of Inorganic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany c Swiss Tropical Institute, Socinstr. 57, CH-4002 Basel, Switzerland d Max Planck Institute for Solid State Research, Heisenbergstraße 1, D-70506 Stuttgart, Germany |
| Abstract: | A broad variety of enantiopure axially chiral 2-aminomethyl-1-(2-oxyphenyl)naphthalenes were prepared via short and efficient synthetic pathways by using the ‘lactone method’ for the regio- and stereoselective construction of the biaryl axis. Their in vitro activity against Trypanosoma cruzi, the causative agent of Chagas' disease, was evaluated. In particular, the M-configured atropisomers, with the 2-oxy function equipped with an O-triflate group, were found to exhibit good antitrypanosomal activities (down to IC50=1.6 μg/mL), combined with low levels of cytotoxicity. |
| Keywords: | Axially chiral biaryls Atropisomerism Asymmetric synthesis Antitrypanosomal activity Chagas' disease |
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