Τομέας ΦΑΡΜΑΚΟΓΝΩΣΙΑΣ ΚΑΙ ΧΗΜΕΙΑΣ ΦΥΣΙΚΩΝ ΠΡΟΪΟΝΤΩΝ
Library of the School of Science

2012-04-06

2012

Τσουκαλάς Κωνσταντίνος

Επίκ. Καθηγητής κ. Νεκτάριος Αληγιάννης (επιβλέπων), Καθηγητής κ. Αλέξιος-Λέανδρος Σκαλτσούνης , Καθηγητής κ. Βασίλειος Ρούσσης

Σχεδιασμός και σύνθεση αναλόγων χαλκονών και αξιολόγηση της βιολογικής τους δράσης

Greek

The aim of this work was the development of synthetic analogues of chalconoids
and investigation of their ability to induce or inhibit angiogenesis and
tyrosinase.
Eleven substituted and non-substituted chalcones, ten diarylopropanes and one
dihydrochalcone were designed and synthesized. The synthesis started from
acetophenones and benzaldehydes via Claisen-Schmidt reaction, giving excellent
yields of chalcones. The latter compounds, upon catalytic hydrogenation in the
presence of Pd/C 10% in ethanol/ethyl acetate (1/1) at 55 psi, are converted to
the corresponding diarylopropanes. In the case of dihydrochalcone, it was
synthesized via Friedel-Crafts reaction, using hydrogenated p-coumaric acid and
resorcinol. All new compounds were fully characterized by spectroscopic methods
and high resolution mass spectrometry. The coumpounds were studied as
angiogenesis inhibitors/inducers on endothelial cells and as inhibitors of the
activity of the tyrosinase enzyme.
The results obtained indicated that diarylopropanes and the dihydrochalcone
were able to inhibit angiogenesis. Chalcones did not demonstrate inhibition
properties. Interestingly, a prenyl diarylopropane in low concentration
induced angiogenesis. Regarding the other biological target, one diarylpropane
showed strong tyrosinase inhibition. The results obtained were very important
to determine the structural and stereoelectronic requirements in the research
of an optimal angiogenetic and tyrosinase inhibitor.

Chalcones, Diarylpropanes, Dihydrochalcone, Tyrosinase, Angiogenesis

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https://pergamos.lib.uoa.gr/uoa/dl/object/1320234