Following our search for antimalarial compounds, novel series of ferrocenyl-substituted pyrrolo[1,2-a]quinoxalines 1-2 were synthesized from ferrocene-carboxaldehyde and tested for their in vitro activity upon the erythrocytic development of Plasmodium falciparum strains with different chloroquine-resistance status. The ferrocenic pyrrolo[1,2-a]quinoxalines 1-2 were prepared in 6 or 9 steps through a Barton-Zard reaction. Promising pharmacological results against FcB1, K1 and F32 strains were obtained with ferrocenyl pyrrolo[1,2-a]quinoxalines 1j-l linked by a bis-(3-aminopropyl)piperazine linker substituted by a nitrobenzyl moiety.
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http://dx.doi.org/10.1016/j.ejmech.2011.03.014 | DOI Listing |
RSC Adv
November 2024
School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University Shihezi 832003 China +86 0993 2057270 +86 0993 2057213.
Pyrrolo[2,3-]quinoxaline derivatives are known to possess antioxidant, anticancer, and antibacterial properties. Here we report the successful synthesis of five derivatives of 3-hydroxy-3-pyrroline-2-one through substitution. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay was employed to evaluate the antioxidant activity of the compounds.
View Article and Find Full Text PDFACS Omega
July 2024
Department of Chemistry, Faculty of Arts and Science, Middle East Technical University, 06800 Ankara, Turkey.
In this paper, we describe an efficient InCl-catalyzed two-component reaction of 1-(2-aminophenyl)pyrroles/indoles and 2-propargyloxybenzaldehydes for the direct synthesis of 12b-benzo[6,7]1,4-oxazepino[4,5-]pyrrolo/indolo[2,1-]quinoxalines. This high atom- and step-economical one-pot process generates three new C/N-C bonds in a single synthetic operation, resulting in the formation of new six- and seven-membered heterocyclic rings. The easy availability of the starting materials, the use of the relatively inexpensive indium catalyst, and the good substrate scope are the salient features of this strategy.
View Article and Find Full Text PDFOrg Biomol Chem
July 2024
Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research, S. A. S. Nagar, Punjab 160062, India.
RSC Adv
June 2024
Medical Analysis Department, Applied Science Faculty, Tishk International University Erbil Kurdistan Region Iraq
A Cu-catalyzed tandem transformation of Ugi adducts through CH/NH bond functionalization reactions was reported for synthesizing a broad spectrum of indolo/pyrrolo-[1,2-]quinoxaline-6/4-carboxamide, 7-indolo[2,3-]quinoline-6-carboxamide, and 1-(cyclohexylamino)-14-indolo[2,3-][1,4]oxazino[4,3-]quinolin-4(3)-one derivatives in moderate to excellent yields. In this protocol the Ugi condensation of aromatic aldehydes, anilines, acids, and isocyanides leads to the formation of bis-amides in methanol at room temperature. This approach employed simple reaction conditions, including Ugi product as starting material, CuI, l-proline as a ligand, and cesium carbonate, in DMSO for 8 h.
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