4th EucheMs chemistry congress

Poster Session 2
s1323
chem. Listy 106, s257–s1425 (2012)
Poster session 2 - organic chemistry
P - 0 9 2 1
BithioPheneSiLAne-BASed dendritiC
MACroMoLeCuLeS: SyntheSiS And ProPertieS
y. LuPonoSov 1 , S. PonoMArenKo 1 , n. rASuLovA 1 ,
n. Surin 1 , e. MALtzev 2 , d. LuPenKo 2 ,
A. MuzAfArov 1
1 Institute of Synthetic Polymeric Materials Russian Academy of
Sciences, Laboratory of Functional Materials for Organic
Electronics and Photonics, Moscow, Russia
2 Institute of Physical Chemistry and Electrochemistry Russian
Academy of Sciences, Laboratory, Moscow, Russia
Dendrimers are unique organic materials, which combine
highly branched regular arrangement of functional organic
moieties within one macromolecule having typical dimensions of
1 to 10 nm. Oligothiophenesilane dendrimers are known for their
efficient molecular antenna effect [1] , as well as intensive
photoluminescence in the violet-blue region, the quantum yields
of which are significantly higher than those measured for their
constituent luminophores themselves [2] . The main drawback of the
high-molecular weight dendrimers is their multistage synthesis,
which limits their practical applications. This problem may be
solved by the synthesis of dendronized polymers. These unique
materials combine the properties of both dendrimers and
polymers. They are currently are under intense investigation with
respect to various applications, including the synthesis of
hierarchically structured materials, catalysis, applications in the
biosciences, such as ion channel mimics and DNA
compactization, as well as optoelectronic applications [3] . We report
here the synthesis and investigation of several generations of
bithiophenesilane-based dendrimers and dendronized polymers [4]
as well as preliminary application of the most perspective
molecules in organic light-emitting diodes.
Acknowledgement: This work was supported by the Program of
President of Russian Federation (grant MK-1567.2011.3) and
by the Presidium of Russian Academy of Sciences
(Program No. 24).
references:
1. Luponosov, Y.N., Ponomarenko, S.A., Surin, N.M.,
Borshchev, O.V., Shumilkina, E.A., Muzafarov, A.M.
Chem. Mater. 2009, 21, 447.
2. Luponosov, Y.N., Ponomarenko, S.A., Surin, N.M.,
Muzafarov. A.M. Org. Lett., 2008, 10, 2753.
3. Frauenrath H. Prog. Polym. Sci. 2005, 30, 144-150.
4. Ponomarenko, S. A., Rasulova, N. N., Luponosov, Y. N.,
Surin, N. M., Buzin, M. I., Leshchiner, I., Peregudova, S. M.,
Muzafarov. A. M. Macromolecules, 2012, 45, 2014.
Keywords: dendronized polymers; dendrimer; luminescence;
4 th EucheMs chemistry congress
P - 0 9 2 2
new CArBoCyCLiC nuCLeoSide AnALoGS
L. MAier 1 , o. hyLSe 1 , K. PAruCh 1
1 Masaryk University, Department of Chemistry, Brno, Czech
Republic
Nucleoside analogs encompass a variety of biologically
active compounds, namely those with antiviral and anticancer
properties. Significant efforts have been invested in order to
prepare nucleoside analogs possessing new structural motifs [1] .
Carbocyclic nucleoside analogs have been particularly attractive
as the tetrahydrofuran moiety can often be replaced with more
metabolically stable carbocycles without significant loss of
activity [2] . Nevertheless, cyclopentane nucleoside analogs
(especially those with the base attached via C-C linkage) are quite
rare and most published syntheses produced only single target
compounds [3] .
Of biologically active carbocyclic nucleoside analogs,
pseudoisocytidine proved active against cytarabine-resistant
leukemias and showed resistance toward deamination mediated by
cytidine deaminase [4] , but its hepatotoxicity (of unknown origin)
in humans halted the clinical progression [5] . We have synthesized
the direct carbocyclic analog of pseudoicytidine and additional
compounds with differently substituted pyrimidine base parts.
In addition, we have developed flexible synthesis of
cyclopentane nucleoside analogs possessing tertiary OH at the
1'-position. Unlike the tetrahydrofuran-containing analogs, the
compounds are chemically robust. Our methodology enables
selective manipulation of individual positions around the
cyclopentane ring.
references:
1. Modified Nucleosides in Biochemistry, Biotechnology and
Medicine; Herdewijn, P.; Ed.; Wiley-VCH, 2008.
2. Lutz, S.; Benner, S. A. Nucleic Acids Res. 1999, 27, 2792.
3. Zhu, X. F. Nucleosides Nucleotides and Nucleic acids,
2000, 19, 651.
4. Burchenal, J. H. et al. Cancer Res. 1976, 36, 1520.
5. Woodcock, T. M. et al. Cancer Res. 1980, 40, 4243.
Keywords: nucleosides; synthetic methods; drug design;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc