Palladium nanoparticles for the synthesis of phenanthridinones and benzo[c]chromenes via C–H activation reaction
Date
2024-06-11Author
Díaz Vázquez, Eva D.
Cuellar, Micaela A.
Heredia, Micaela D.
Barolo, Silvia M.
González Bakker, Aday
Padrón, José M.
Budén, María E.
Martín, Sandra E.
Uberman, Paula M.
ORCID
https://orcid.org/0000-0002-5688-4162https://orcid.org/0000-0002-9792-5194
https://orcid.org/0000-0002-2424-3299
https://orcid.org/0000-0003-1211-9968
Metadata
Show full item recordAbstract
In the present work, derivatives of phenanthridine-6(5H)-ones and benzo[c]chromenes were efficiently
prepared through an intramolecular C–H bond functionalization reaction catalyzed by photochemically
synthesized Pd-PVP nanoparticles. The heterocycles were obtained via intramolecular arylation of the
corresponding N-methyl-N-aryl-2-halobenzamide or aryl-(2-halo)benzyl ethers using K2CO3 as base in
a mixture of H2O: DMA as solvent without additives or ligands. High yields of the heterocyclic
compounds were achieved (up to 95%) using a moderately low catalyst loading (1–5 mol%) under an air
atmosphere at 100 °C. The reaction exhibited very good tolerance to diverse functional groups (OMe,
Me, tBu, Ph, OCF3, CF3
, F, Cl, –CN, Naph), and both bromine and iodine substrates showed great
reactivity. Finally, the in vitro antiproliferative activity of phenanthridine-6(5H)-ones and benzo[c]
chromenes was evaluated against six human solid tumor cell lines. The more active compounds exhibit
activity in the low micromolar range. 1-Isopropyl-4-methyl-6H-benzo[c]chromene was identified as the
best compound with promising values of activity (GI50 range 3.9–8.6 mM). Thus, the benzochromene
core was highlighted as a novel organic building block to prepare potential antitumor agents.
xmlui.dri2xhtml.METS-1.0.item-citation
Díaz-Vázquez, E. D., Cuellar, M. A., Heredia, M. D., Barolo, S. M., González-Bakker, A., Padrón, J. M., ... & Uberman, P. M. (2024). Palladium nanoparticles for the synthesis of phenanthridinones and benzo [c] chromenes via C–H activation reaction. RSC advances, 14(26), 18703-18715.
Other links
https://pubs.rsc.org/en/content/articlehtml/2024/ra/d4ra02835jhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11166021/
https://pubmed.ncbi.nlm.nih.gov/38863826/
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