Revistas
Revista:
MOLECULES
ISSN:
1420-3049
Año:
2022
Vol.:
27
N°:
3
Págs.:
982
The reactivity of thiophene in Diels-Alder reactions is investigated with different maleimide derivatives. In this paper, we have synthesized for the first time the Diels-Alder adducts of thiophene at room temperature and atmospheric pressure. Maleimido-thiophene adducts were promoted by AlCl3. The effects of solvent, time, temperature and the use of different Lewis acids were studied, showing dramatic effects for solvent and Lewis acid. Furthermore, the catalysis with AlCl3 is highly stereoselective, preferably providing the exo form of the adduct. Additionally, we also discovered the ability of AlCl3 to catalyze the arylation of maleimides to yield 3-aryl succinimides in a straightforward manner following a Friedel-Crafts-type addition. The inclusion of a selenocyanate group contributes to the cytotoxic activity of the adduct. This derivatization (from compound 7 to compound 15) results in an average GI(50) value of 1.98 mu M in the DTP (NCI-60) cell panel, resulting in being especially active in renal cancer cells.
Revista:
ANTIOXIDANTS
ISSN:
2076-3921
Año:
2021
Vol.:
10
N°:
5
Págs.:
777
A series of 30 novel N,N disubstituted selenoureas were synthesized, characterized, and
their antioxidant ability was tested using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,20-azinobis(
3-ethylbenzthiazoline-6-sulfonic acid (ABTS) assays. Additionally, their cytotoxic activity was
tested in vitro in a panel of three different cancer (breast, lung and colon) and two normal cell lines.
Each selenourea entity contains a para-substituted phenyl ring with different electron-withdrawing
and electron-donating groups, and different aliphatic and aromatic nuclei. All of the synthesized
selenoureas present antioxidant capacity at high concentrations in the DPPH assay, and three of them
(2b, 2c and 2d) showed greater radical scavenging capacity than ascorbic acid at lower concentrations.
These results were confirmed by the ABTS assay, where these novel selenoureas present even higher
antioxidant capacity than the reference compound Trolox. On the other hand, 10 selenoureas present
IC50 values below 10 M in at least one cancer cell line, resulting in the adamantyl nucleus (6a¿
6e), the most interesting in terms of activity and selectivity. Outstanding results were found for
selenourea 6c, tested in the NCI60 cell line panel and showing an average GI50 of 1.49 M for the
60 cell lines, and LC50 values ranging from 9.33 M to 4.27 M against 10 of these cancer cell lines.
To gain insight into its anticancer activity mechanism, we investigated the cell cycle progression
of the promising c
Otros (PIUNA, fundaciones, contratos…)
Título:
Diseño y desarrollo preclínico de nuevas moléculas híbridas de selenio como agentes antitumorales
Código de expediente:
2018-19
Financiador:
UNIVERSIDAD DE NAVARRA
Convocatoria:
2020 Convocatoria PIUNA
Fecha de inicio:
01/09/2018
Fecha fin:
31/08/2021
Importe concedido:
16.500,00€