366018-60-2Relevant academic research and scientific papers
Quinoxaline-PABA bipartite hybrid derivatization approach: Design and search for antimicrobial agents
Patel, Harun M.,Bhardwaj, Varun,Sharma, Poonam,Noolvi, Malleshappa N.,Lohan, Sandeep,Bansal, Sumit,Sharma, Amit
, p. 562 - 568 (2019/03/06)
In an attempt to find a new class of antimicrobial agents, in the present study we report the synthesis of bipartite hybrid styryl derivatives of quinoxaline containing para-aminobenzoic acid (PABA) and their biological evaluation as antimicrobial agents. The series of new substituted styryl based derivatives 5(a–k) were evaluated for antimicrobial potential against various bacteria including Staphylococcus aureus, Vibrio cholerae, Escherichia coli, Bacillus subtilis, Escherichia coli, Mycobacterium smegmatis, Pseudomonas aeruginosa and fungi; C. albicans, with ampicillin and amphotericin B as standards. Similarly these compounds were also screened for anti-cancer activity using MCF-7 cell line. Among the synthesized compounds, 5(c) was observed to be the most active compound against various strains with MIC in a range of 7.9–31 μM of the series and compound 5i came out with significant anti-cancer activity with IC50 value of 7 μM.
Multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones in an aqueous medium
da Costa, Erivaldo P.,Coelho, Sara E.,de Oliveira, André H.,Araújo, Renata M.,Cavalcanti, Livia N.,Domingos, Josiel B.,Menezes, Fabrício G.
supporting information, p. 3961 - 3964 (2018/09/27)
A multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones is described. Sequential reactions of o-phenylenediamine with sodium pyruvate and aldehydes in 20% aqueous acetic acid containing sodium acetate provided the target products in good to high yields. The reaction is proposed to proceed via initial condensation of the diamine and pyruvate partners followed by an aldol condensation-type mechanism.
Studies on the synthesis of 2-phenylsulphonyl-3-styrylquinoxalines
Krishnan,Chowdary,Dubey,Vijaya
, p. 565 - 573 (2007/10/03)
o-Phenylenediamine 1 is condensed with pyruvic acid or sodium pyruvate to yield 3-methylbenzo-1H-dihydropyrazine-2-one 2. The latter on condensation with aromatic aldehydes give 3-styrylquinoxaline-1H-2-one 3. Reaction of 3 with POCl3 in the presence of catalytic amount of DMF yields 2-chloro-3-styrylquinoxaline 4, which on reaction with thiophenol in the presence of triethylamine in methanol gives 2-phenylthio-3-styrylquinoxaline 5. Oxidation of 5 with H2O2 in the presence of acetic anhydride affords 2-phenylsulphonyl-3-styrylquinoxaline 6. 6 has also been prepared directly from 4 by reaction with sodium benzenesulphinate under phase transfer conditions. In an alternate approach to the synthesis of title compound. 2 is treated with POCl3 in DMF to obtain the known 2-chloro-3-methylquinoxaline 7. Reaction of 7 with thiophenol in the presence of triethylamine in methanol gives 2-methyl-3-phenylthioquinoxaline 8. Oxidation of 8 with H2O2 in Ac2O affords 2-methyl-3-phenylsulphonylquinoxaline 9. 9 was also prepared in an alternate method from 7 by reaction with sodium benzenesulphinate, 9 on reaction with aromatic aldehydes yields the title compounds 6.
