4th EucheMs chemistry congress

Poster Session 1
s1026
chem. Listy 106, s587–s1425 (2012)
Poster session 1 - organic chemistry
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towArdS A LiGht driven Proton PuMP
B. heSSeLer 1 , M. zindLer 1 , u. LüninG 1
1 Otto-Diels-Institut, Organische Chemie, Kiel, Germany
Light driven uphill transport of protons is an essential
process in nature. In the photosynthetic apparatus, light energy is
used to pump protons across a cell membrane.
In our model system, the proton transfer is realized by a
photo-switchable acid, such as 2-(2,4-dinitrobenzyl)pyridine
(DNBP), attached to a [2]rotaxane. Upon irradiation, the
photo-switchable acid tautomerizes to a more acidic form and
protonates the macrocycle. Due to electrostatic repulsion with a
permanent positive charge on the axle, the macrocycle moves
along the axle. After the release of the proton, the macrocycle
returns to the starting position.
For the realization of this model system, several novel
DNBP derivatives were successfully synthesized including the
development of a new method to obtain di- and trinitrobenzyl
substituted pyridine derivatives. [1] Furthermore, several axles
and macrocycles [2] were synthesized and assembled to yield a
[2]rotaxane.
references:
1. A. Frej, C. Goeschen, C. Näther, U. Lüning, R. Herges,
J. Phys. Org. Chem. 2010, 23, 1093-1098.
2. U. Lüning, E. Mak, M. Zindler, B. Hartkopf, R. Herges,
Eur. J. Org. Chem. 2010, 4932-4940.
Keywords: Supramolecular chemistry; Rotaxanes; Proton
transport;
4 th EucheMs chemistry congress
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SyntheSiS And ChArACteriSAtion of Proved
And PotentiAL MetABoLiteS of MePhedrone
M. hiML 1 , i. LinhArt 1
1 Institute of Chemical Technology Prague, Department of
Organic Chemistry, Prague 6, Czech Republic
In recent years, a new class of designer drugs has appeared
on the drug of abuse market in many countries. Global increase
in the abuse of 4'-methylmethcathinone (mephedrone) and
related compounds created a requirement for full chemical
characterisation of these products and their metabolites. [1, 2] In this
work we present full synthetic and chemical characterisation data
for proved and potential metabolites of mephedrone.
Starting from 1-(p-tolyl)propan-1-one [3,4] several
mephedrone derivatives, mainly, 1-(4-(hydroxymethyl)phenyl)-
-2-(methylamino)propan-1-one, 2-amino-1-(p-tolyl)propan-1-one,
2-amino-1-(4-(hydroxymethyl)phenyl)propan-1-one, 2-amino-1-
-(p-tolyl)propan-1-ol, 4-(1-hydroxy-2-(methylamino)propyl)benzoic
acid and some others were prepared by step-by-step syntheses.
All the above mentioned mephedrone metabolites were
synthesised as hydrochloride salts and will be used as synthetic
standards for metabolism studies. Reaction conditions as well as
various possible synthetic approaches to mephedrone metabolites
will be discussed.
Acknowledgement: Financial support by grant VG2VS/200
from the Ministry of Interior of the Czech Republic is gratefully
acknowledged.
references:
1. Anal. Bioanal. Chem. (2010), 397, 1225–1233
2. J. Pharmaceut. Biomed. Anal. (2011), 56, 246–255
3. Tetrahedron: Asymmetry (2001), 12, 719–724
4. Tetrahedron: Asymmetry (2001), 12, 3417–3422
Keywords: mephedrone; metabolism;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc