Synthesis of New Quinoxaline Derivatives

Makhloufi, A.; Baitiche, Milad; Merbah, M.; Benachour, Djafer

doi:10.1080/00397911.2010.519091

Cited by 6 publications

(3 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In most cases, the quinoxaline thiol 55 was commercially available but in a few examples (R 1 = CF 3 and Et) we prepared this thiol by converting congeners 54 (R 1 = CF 3 and Et) using P 2 S 5 and pyridine. 37 Compound 54 where R 1 = CF 3 was prepared by reaction of o -phenylenediamine with ethyl trifluoropyruvate 38 and 54 where R 1 = Et is commercially available.…”

mentioning

confidence: 99%

Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress

Loughran

Han

Wrobel

et al. 2016

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

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.

show abstract

mentioning

confidence: 99%

Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress

Loughran

Han

Wrobel

et al. 2016

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

show abstract

“…3. As described in the literature, 3 could be easily prepared from the condensation of 2-aminoaniline (1) with ethyl 2-oxopropanoate under acidic conditions to get 3-methylquinoxalin-2-one (2) in 78% yield [15], then 2 is converted to 3 by a thiation in 87% yield, using phosphorus pentasulfide in pyridine under reflux conditions during 6 h (Scheme 1) [16].…”

Section: Resultsmentioning

confidence: 99%

Cyclisation reaction between 3-methylquinoxaline-2-thione and benzaldehydes into 3-benzyl-2-aryl-thieno[2,3-b]quinoxaline promoted by Brønsted acids

Saoudi

Téniou

Debache

et al. 2015

Comptes Rendus. Chimie

View full text Add to dashboard Cite

International audience2,3-Disubstituted thieno[2,3-b]quinoxaline derivatives have been synthetized through the condensation of commercially available benzaldehydes with 3-methylquinoxaline-2-thione in EtOH using Brønsted acids, namely sulfuric or hydrochloric acids. A wide range of substituted benzaldehydes has been used, allowing the formation of 3-(substituted)benzyl-2-arylthieno[2,3-b]quinoxalines in high yields in only one ste

show abstract

“…Finally, to explore the general synthetic applicability of quinoxalin-2-ones, we have synthesized a range of quinoxalin-2-one derivatives with potential application in drug discovery. Initially, quinoxalin-2-one 7a was converted into 2-chloro-3-phenylquinoxaline (13) by treatment with PO-Cl 3 under neat conditions at elevated temperature 11 and Scheme 3 Substrate scope of the reaction. Reagents and conditions: dibromoketone 6 (1 mol), cyclohexyl-1,2-diamine 8 (1 mol), triethylamine (3 mol), DMSO (6 mL), 75 °C, 2 h.…”

Section: Scheme 4 Gram-scale Reactionmentioning

confidence: 99%