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From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines.

Authors :
Lassagne, Frédéric
Langlais, Timothy
Caytan, Elsa
Limanton, Emmanuelle
Paquin, Ludovic
Boullard, Manon
Courtel, Coline
Curbet, Idriss
Gédéon, Clément
Lebreton, Julien
Picot, Laurent
Thiéry, Valérie
Souab, Mohamed
Baratte, Blandine
Ruchaud, Sandrine
Bach, Stéphane
Roisnel, Thierry
Mongin, Florence
Bunce, Richard A.
Source :
Molecules; Nov2018, Vol. 23 Issue 11, p2961, 1p, 7 Diagrams, 5 Charts, 1 Graph
Publication Year :
2018

Abstract

2,3-Diphenylated quinoxaline, pyrido[2,3-b]pyrazine and 8-bromopyrido[3,4-b]pyrazine were halogenated in deprotometalation-trapping reactions using mixed 2,2,6,6-tetramethyl piperidino-based lithium-zinc combinations in tetrahydrofuran. The 2,3-diphenylated 5-iodo- quinoxaline, 8-iodopyrido[2,3-b]pyrazine and 8-bromo-7-iodopyrido[3,4-b]pyrazine thus obtained were subjected to palladium-catalyzed couplings with arylboronic acids or anilines, and possible subsequent cyclizations to afford the corresponding pyrazino[2,3-a]carbazole, pyrazino[2′,3′:5,6] pyrido[4,3-b]indole and pyrazino[2′,3′:4,5]pyrido[2,3-d]indole, respectively. 8-Iodopyrido[2,3-b] pyrazine was subjected either to a copper-catalyzed C-N bond formation with azoles, or to direct substitution to introduce alkylamino, benzylamino, hydrazine and aryloxy groups at the 8 position. The 8-hydrazino product was converted into aryl hydrazones. Most of the compounds were evaluated for their biological properties (antiproliferative activity in A2058 melanoma cells and disease-relevant kinase inhibition). [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14203049
Volume :
23
Issue :
11
Database :
Complementary Index
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
133158377
Full Text :
https://doi.org/10.3390/molecules23112961