(János Bolyai Research Scholarship (BO/00158/22/5))
Szakterületek:
Farmakológia és gyógyszerészet
Szerveskémia
Szintetikus szerveskémia
The reaction between glycine-type aminonaphthol derivatives substituted with 2- or
1-naphthol and indole or 7-azaindole has been tested. Starting from 2-naphthol as
a precursor, the reaction led to the formation of ring-closed products, while in the
case of a 1-naphthol-type precursor, the desired biaryl ester was isolated. The synthesis
of a bifunctional precursor starting from 5-chloro-8-hydroxyquinoline, morpholine,
and ethyl glyoxylate via modified Mannich reaction is reported. The formed Mannich
base 10 was subjected to give bioconjugates with indole and 7-azaindole. The effect
of the aldehyde component and the amine part of the Mannich base on the synthetic
pathway was also investigated. In favor of having a preliminary overview of the structure-activity
relationships, the derivatives have been tested on cancer and normal cell lines. In
the case of bioconjugate 16, as the most powerful scaffold in the series bearing indole
and a 5-chloro-8-hydroxyquinoline skeleton, a potent toxic activity against the resistant
Colo320 colon adenocarcinoma cell line was observed. Furthermore, this derivative
was selective towards cancer cell lines showing no toxicity on non-tumor fibroblast
cells.
