2000
DOI: 10.1002/jhet.5570370541
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Synthesis and properties of some 2,3‐disubstituted 6‐fluoro‐7‐(4‐methyl‐1‐piperazinyl)quinoxalines

Abstract: The 2,3‐disubstituted 6‐fluoro‐7‐(4‐methyl‐1‐piperazinyl)‐quinoxalines (3–11) were synthesized for bioassay via reaction of 1.2‐diamino‐4‐fluoro‐5‐(4‐methyl‐1‐piperazinyl)benzene (2) with the appropriate 1,2‐dicarbonyl compounds. However, none of the tested compounds 3–11 showed significant in vitro activ ity against E. coli ATCC11229, S. aureus ATCC6538 and C.albicans SATCC10231.

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Cited by 13 publications
(5 citation statements)
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“…Having successfully isolated the bis(isobenzofuran) cis-1 bisadduct 4b possessing the one-atom (CH 2 ) linker, we became interested in the possibility of forming bis(isobenzofuran) cis-1 bisadducts featuring longer linkers. After considering many of the options available for a two-atom tether, we chose to use the quinoxaline-2,3-diyl linker because 2,3-bisfurylquinoxaline can be readily prepared from commercially available furfural in a few steps and on a large scale . In principle, 2,3-bisfurylquinoxaline can be used as a building block for preparing a number of other bis(isobenzofuran) precursors because the C5 position of the furyl group is readily functionalized, e.g., through Vilsmeier−Haack formylation .…”
Section: Resultsmentioning
confidence: 99%
“…Having successfully isolated the bis(isobenzofuran) cis-1 bisadduct 4b possessing the one-atom (CH 2 ) linker, we became interested in the possibility of forming bis(isobenzofuran) cis-1 bisadducts featuring longer linkers. After considering many of the options available for a two-atom tether, we chose to use the quinoxaline-2,3-diyl linker because 2,3-bisfurylquinoxaline can be readily prepared from commercially available furfural in a few steps and on a large scale . In principle, 2,3-bisfurylquinoxaline can be used as a building block for preparing a number of other bis(isobenzofuran) precursors because the C5 position of the furyl group is readily functionalized, e.g., through Vilsmeier−Haack formylation .…”
Section: Resultsmentioning
confidence: 99%
“…4-Fluoro-5-(4-piperazinyl)-1,2-diaminobenzene has recently been proved to be a valuable intermediate for the synthesis of various benzimidazole derivatives of biological interest, for example, as anticancer agents and bactericides [17]. Furthermore, ferrocenyl-based complexes with 5-fluoro-6-(4-substituted-1-piperazinyl)benzimidazoles have been reported.…”
Section: Introductionmentioning
confidence: 99%
“…The introduction of fluorine and piperazine appendages played a vital role in enhancing the antimicrobial activities of the quinolone drugs, e.g., ciprofloxacin ® ( 1 ) (Figure 1), the most active antibiotic drug on the market [12]. Similarly, we have successfully synthesized a variety of heterocyclic systems incorporating fluorine and piperazine moieties, such as quinoxaline [13] ( 2 ), benzimidazole [14] ( 3 ), quinazolinone [15] ( 4 ), and recently benzothiazole [16] ( 5 ). Some derivatives of our systems showed very promising biological activities, which were attributed to the presence of both appendages.…”
Section: Introductionmentioning
confidence: 99%