6323-89-3Relevant 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.
Radical Ions of 3-Styryl-quinoxalin-2-one Derivatives Studied by Pulse Radiolysis in Organic Solvents
Skotnicki, Konrad,De La Fuente, Julio R.,Ca?ete, álvaro,Berrios, Eduardo,Bobrowski, Krzysztof
, p. 4051 - 4066 (2018/04/20)
The absorption-spectral and kinetic behaviors of radical ions and neutral hydrogenated radicals of seven 3-styryl-quinoxalin-2(1H)-one (3-SQ) derivatives, one without substituents in the styryl moiety, four others with electron-donating (R = -CH3/su
Synthesis and in vivo diuretic activity of some new benzothiazole sulfonamides containing quinoxaline ring system
Husain, Asif,Madhesia, Diwakar,Rashid, Mohd,Ahmad, Aftab,Khan, Shah Alam
, p. 1682 - 1689 (2016/10/09)
A series of new 6-substituted-N-[3-{2-(substituted phenyl)-ethenyl} quinoxaline-2(1H)-ylidene]-1,3-benzothiazole-2-amine (4a–f) were designed and synthesized by condensing 2-amino-benzothiazole-6-sulfonic acid amide (1) with chalcones of quinoxaline-2-one (3a–f) in a hope to obtain promising and a new class of diuretic agents. Structures of all the newly synthesized compounds were characterized by spectral data and elemental analysis. The pharmacological studies in experimental rats indicates that compound 4c possesses excellent in vivo diuretic activity of 1.13 and appears to be a better diuretic agent than the reference drugs, acetazolamide (1.0) and urea (0.88). Insight of the binding mode of the synthesized compounds (ligand) into the binding sites of carbonic anhydrase enzyme (PDF code: 4KUV) was provided by docking studies, performed with the help of Maestro 9.0 docking software. Further pharmacokinetic and toxicological studies are needed to confirm the safety of compound 4c which emerged as a lead diuretic compound.
A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
Mamedov, Vakhid A.,Zhukova, Nataliya A.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Beschastnova, Tat'Yana N.,Adgamova, Dil'Bar I.,Samigullina, Aida I.,Latypov, Shamil K.
, p. 1403 - 1416 (2013/02/23)
A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.
Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives: Search for anticancer agent
Noolvi, Malleshappa N.,Patel, Harun M.,Bhardwaj, Varun,Chauhan, Ankit
, p. 2327 - 2346 (2011/06/25)
The synthesis of some 2-furano-4(3H)-quinazolinones, diamides (open ring quinazolines), quinoxalines and their biological evaluation as antitumor agents using National Cancer Institute (NCI) disease oriented antitumor screen protocol are investigated. Among the synthesize compounds, seventeen compounds were granted NSC code and screened at National Cancer Institute (NCI), USA for anticancer activity at a single high dose (10-5 M) in full NCI 60 cell panel. Among the selected compounds, 3-(2-chloro benzylideneamine)-2- (furan-2-yl) quinazoline-4(3h)-one 21 was found to be the most active candidate of the series at five dose level screening against Ovarian OVCAR-4 and Non-small cell lung cancer NCI-H522 with GI50 1.82 & 2.14 μM respectively. Rational approach and QSAR techniques enabled the understanding of the pharmacophoric requirement for quinazoline, diamides and quinoxaline derivatives.
Synthesis, characterization and biological evaluation of some heterocyclic compounds containing ethoxyphthalimide moiety via key intermediate 6-chloro 1,3 benzothiazole 2-amine
Sain, Devendra Kr.,Thadhaney, Bhawana,Joshi, Ajit,Hussain, Nasir,Talesara, Ganpat L.
experimental part, p. 818 - 825 (2011/02/23)
New and simple synthetic methods for the synthesis of ethyl 8-chloro-4(4-substitutedphenyl)-2-[(N-ethoxyphthalimido)amino]-4H-pyrimido[2, 1-b][1,3] benzothiazole-3-carboxylate 5a-d and 6-chloro-N-[3-{2-(4- substitutedphenyl)ethenyl}-1-N-ethoxyphthalimidoquinoxalin-2(1N)-ylidene]-1, 3-benzothiazol-2-amine 10a-d are described. 4-Chloroaniline 1 is converted to 6-chloro-1,3-benzothiazol-2-amine 2 by reaction with KSCN and Br2. Compound 2 acts as key intermediate for both the series of final compounds. In one pathway, 2 is converted to corresponding pyrimidothiazoles 4a-d by treatment with ethyl arylidinecyanoacetate 3a-d, which on condensation with phthalimidoxyethyl bromide 6 gives 5a-d. In a parallel route, reaction of 2 with 3-[2-(4-substituted phenyl)ethenyl]quinoxalin-2(1H)-one 8a-d affords 6-chloro-iV-[3-{2-(4-substituted phenyl)ethenyl} quinoxalin-2(1H)-ylidene]-1,3- benzothiazol-2-amine 9a-d which on condensation with phthalimidoxyethyl bromide 6, yields final compound 10a-d. Structure elucidation is accomplished by elemental analysis and spectral data of the synthesized compounds. Final compounds 5a-d and 10a-d have been screened in vitro for their antimicrobial activity against different strains of bacteria and fungi.
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.
