N-ferrocenylpyridazinones and new organic analogues: synthesis, cyclic voltammetry, DFT analysis and in vitro antiproliferative activity associated with ROS-generation
  • Metaadatok
Tartalom: http://real.mtak.hu/74294/
Archívum: MTA Könyvtár
Gyűjtemény: Status = Published


Type = Article
Cím:
N-ferrocenylpyridazinones and new organic analogues: synthesis, cyclic voltammetry, DFT analysis and in vitro antiproliferative activity associated with ROS-generation
Létrehozó:
Jernei, Tamás
BĹ‘sze, Szilvia
SzabĂł, Rita
Hudecz, Ferenc
Majrik, Katalin
Csámpai, Antal
Kiadó:
Elsevier
Dátum:
2017-09-13
Téma:
QD04 Organic chemistry / szerves kémia
QH3011 Biochemistry / biokémia
Tartalmi leírás:
Employing an optimized Pd-catalyzed cross-coupling reaction promoted by CuI, novel N-ferrocenylpyridazinones
along with N-phenyl- and N-(2-pyridyl) analogues were synthesized from readily available
heterocyclic precursors, iodoferrocene, iodobenzene and 2-bromopyridine. With exception of the ferrocenylation
of 6-ferrocenylpyridazin-3(2H)-one yielding both N- and O-substituted products, the
studied reactions exclusively afforded N-aryl lactams. The novel compounds exhibited cytotoxicity towards
HEPG2 and HT-29 human malignant cells under in vitro conditions. The measured IC50 values
supplemented with the results of cyclic voltammetry and DFT calculations suggest that the cytotoxic
activity of the N- and O-ferrocenyl-substituted derivatives and the decreased effect of the N-phenyl
analogues seem to be at least partly associated with the potential to generate reactive oxygen species
(ROS). This interpretation, allowing the prediction of characteristic substituent-dependent SAR, was
supported by the results of related studies on the practically inactive N-(2-pyridyl)pyridazinones
assumed to be present in protonated chelate forms with highly a decreased propensity to undergo
ionization.
Nyelv:
magyar
Típus:
Article
PeerReviewed
info:eu-repo/semantics/article
Formátum:
text
Azonosító:
Jernei, Tamás and Bősze, Szilvia and Szabó, Rita and Hudecz, Ferenc and Majrik, Katalin and Csámpai, Antal (2017) N-ferrocenylpyridazinones and new organic analogues: synthesis, cyclic voltammetry, DFT analysis and in vitro antiproliferative activity associated with ROS-generation. TETRAHEDRON, 73. pp. 6181-6192. ISSN 0040-4020
Kapcsolat:
https://10.1016/j.tet.2017.09.015
doi: 10.1016/j.tet.2017.09.015