13297-35-3Relevant articles and documents
Synthesis of 3-alkylquinoxalin-2(1H)-ones via Grignard reaction
Kalinin,Mamedov
, p. 1098 - 1101 (2009)
A two-step procedure has been developed for the synthesis of 3-alkylquinoxalin-2(1H)-ones from o-phenylenediamine and ethyl 2-oxoalkanoates prepared by the Grignard reaction of diethyl oxalate with alkyl bromides. Analogous reaction with α,ω-dibromoalkanes instead of alkyl bromides leads to the formation of 3,3'-(alkane-α,ω-diyl)di[quinoxalin-2(1H) -ones].
Lithiation and Side-Chain Substitution of 3-Alkyl-1H-quinoxalin-2-ones
Smith, Keith,El-Hiti, Gamal A.,Mahgoub, Safaa A.
, p. 2345 - 2348 (2003)
3-Methyl-1H-quinoxalin-2-one has been doubly lithiated with n-butylithium at -78° C in THF. The dilithio reagent thus obtained reacts with various electrophiles (iodomethane, iodoethane, D2O, benzaldehyde, benzophenone, cyclohexanone) to give modified 3-substituted 1H-quinoxalin-2- ones in good yields. In the reaction of the dilithio reagent with phenyl isothiocyanate the product was a tautomer of the simple substitution product. Reaction of the dilithio reagent with iodine gives an oxidatively dimerised product instead of the 3-iodomethyl derivative. Lithiations of 3-ethyl-and 3-propyl-1H-quinoxalin-2-ones, followed by reactions with representative electrophiles (benzaldehyde, benzophenone, cyclohexanone), behaved in a similar manner to give the corresponding modified 3-substituted derivatives in good yields.
Synthesis of potential chemotherapic quinoxalinone derivatives by biocatalysis or microwave-assisted Hinsberg reaction
Gris, Javier,Glisoni, Romina,Fabian, Lucas,Fernández, Beatriz,Moglioni, Albertina G.
, p. 1053 - 1056 (2008)
In recent years, great efforts have been dedicated to the design of compounds acting as selective inhibitors of the HIV-1 reverse transcriptase (RT). Due to the promissory results previously attained with some quinoxaline derivatives, we aimed to improve the specific standard Hinsberg synthetic pathway by means of biocatalysis or microwave (MW) irradiation. Both techniques rendered the products in very good yields. However, employing the microwave-assisted organic synthesis (MAOS), in the absence of solvent, the same reactions may be completed in minutes. Some of these quinoxalinone derivatives exhibited good inhibitor activity against some human tumoral cells and the lymphoma related to HIV-1.
Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress
Loughran, H. Marie,Han, Ziying,Wrobel, Jay E.,Decker, Sarah E.,Ruthel, Gordon,Freedman, Bruce D.,Harty, Ronald N.,Reitz, Allen B.
supporting information, p. 3429 - 3435 (2016/07/21)
We prepared a series of quinoxalin-2-mercapto-acetyl-urea analogs and evaluated them for their ability to inhibit viral egress in our Marburg and Ebola VP40 VLP budding assays in HEK293T cells. We also evaluated selected compounds in our bimolecular complementation assay (BiMC) to detect and visualize a Marburg mVP40–Nedd4 interaction in live mammalian cells. Antiviral activity was assessed for selected compounds using a live recombinant vesicular stomatitis virus (VSV) (M40 virus) that expresses the EBOV VP40 PPxY L-domain. Finally selected compounds were evaluated in several ADME assays to have an early assessment of their drug properties. Our compounds had low nM potency in these assays (e.g., compounds 21, 24, 26, 39), and had good human liver microsome stability, as well as little or no inhibition of P450 3A4.
