4th EucheMs chemistry congress

Poster Session 2
s1301
chem. Listy 106, s257–s1425 (2012)
Poster session 2 - organic chemistry
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noveL APProACh to SyntheSiS of
CALix[4]Arene reCePtorS
o. hudeCeK 1 , P. CurinovA 2 , J. BudKA 1 , v. eiGner 3 ,
P. LhotAK 1
1 Institute of Chemical Technology Prague, Department of
Organic Chemistry, Prague 6, Czech Republic
2 Institute of Chemical Process Fundamentals of the ASCR v. v.
i, Department of Organic Synthesis and Analytical Chemistry,
Prague, Czech Republic
3 Institute of Chemical Technology Prague, Department of Solid
State Chemistry, Prague 6, Czech Republic
Calix[4]arenes are widely used as platforms for synthesis of
receptors acting in host-guest chemistry. The structure of
calixarene molecule allows interactions with all types of substrates
(soft or hard metal cations, anions and even neutral molecules). [1]
Due to various shapes of anions and their solvent-dependent
stability, the most sophisticated design is required for their
effective binding. [2]
In this research, a novel regioselective derivatisation [3] of
calix[4]arene skeleton has been developed and optimized. This
multi-step synthetic procedure leads to interesting derivatives with
so far almost inaccessible substitution pattern. A subsequent
modification enables to prepare precursors for ureido-based anion
receptors fixed in a cone and a partial cone conformation, and for
versatile receptors which adopt a 1,2-alternate conformation.
Some of them have been synthesized and used for the
complexation experiment. The results as well as the synthetic
approach will be presented.
Acknowledgement: This research is supported by the Czech
Science Foundation (P207/12/2027) and by financial support
from specific university research (MSMT No 21/2012).
references:
1. Gutsche, C. D. Calixarenes An Introduction: Monographs
in Supramolecular Chemistry.
2. Stibor, I.; Budka, J.; Michlova, V.; Tkadlecova, M.;
Pojarova, M.; Curinova, P.; Lhotak, P. New J. Chem.,
2008, 32, 1957-1607.
3. a) Hudecek, O.; Curinova, P.; Budka, J.; Lhotak, P.
Tetrahedron, 2011, 67, 5213-5218.
b) Hudecek, O.; Budka, J.; Eigner, V.; Lhotak, P.
Tetrahedron, 2012, 68, 4187-4193.
Keywords: calix[4]arenes; host-guest chemistry;
4 th EucheMs chemistry congress
P - 0 8 7 7
Steroid ProBeS for the Study of trAnSPort
in A LivinG oBJeCtS
h. ChodounSKá 1 , v. KAPrAS 2 , B. SLAvíKová 3 ,
e. Kudová 3 , L. rAMBouSeK 4 , K. vALeS 5 ,
v. vyKLiCKý 6 , L. Jr. vyKLiCKý 6
1 Institute of Organic Chemistry and Biochemistry AS CR v.v.i.,
Neuroprotectives, Praha 6, Czech Republic
2 Institute of Organic Chemistry and Biochemistry AS CR v.v.i.,
Chemistry of Natural Products, Praha 6, Czech Republic
3 Institute of Organic Chemistry and Biochemistry AS CR v.v.i.,
Neuroprotectives, Praha 6, Czech Republic
4 ICT Prague, Dept. of Organic Technology, Praha 6,
Czech Republic
5 Institute of Physiology AS CR v.v.i., Dept. of Neurophysiology
of Memory, Praha 4, Czech Republic
6 Institute of Physiology AS CR v.v.i., Dept. of Cellular
Neurophysiology, Praha 4, Czech Republic
Steroids and steroid-like compounds are important
molecules for many living organisms. They act as a building
blocks of membranes, take part in the digestion, and in the
signaling pathways. Although many of the steroid roles have been
already understood; a lot of them are continuously being explored.
One example of new and attractive avenues of investigation is the
research of the synthesis and action of neurosteroids in the brain.
Recent development in the methodologies of the biological
processes allows revealing roles of neurosteroids more
straightforward. However, these new methods demand effective
molecular standards and probes.
We have prepared steroid molecules labeled with isotopes,
fluorescent, or photoactive moieties. These probes were used for
the assessment of pharmacokinetics of steroidal neuroprotectives
and for the study of their transport to the neurons.
Keywords: steroids; isotopic labeling; fluorescent probes;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc