Synthesis of potential chemotherapic quinoxalinone derivatives by biocatalysis or microwave-assisted Hinsberg reaction

Gris, Javier H; Glisoni, Romina Julieta; Fabián, Lucas; Fernández, Beatriz; Moglioni, Albertina G.

doi:10.1016/j.tetlet.2007.11.204

Cited by 70 publications

(42 citation statements)

References 10 publications

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“…One-pot efficient green synthesis of 1,4-dihydroquinoxaline-2,3-dione derivatives has reported by potential pharmacophore 1,4-dihydroquinoxaline-2,3-dione has been achieved in a one-pot reaction at room temperature from substituted o-phenylene diamine and oxalic acid under solvent free conditions by a simple grinding method. Thermal and powder X-ray diffraction analysis was carried out for some crystals [54]. …”

Section: Synthesis Of Quinoxalinesmentioning

confidence: 99%

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Synthetic Methods and Exploring Biological Potential of Various Substituted Quinoxalin-2-one Derivatives

2016

European Reviews of Chemical Research

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Substituted quinoxaline have considerable interest in chemistry, biology and pharmacology. Quinoxaline derivatives are capable with variety of biological activities and possess different biological activities, of which the most potent are anti-microbial, analgesic and anti-inflammatory activities. It facilitated the researchers to develop various methods for their synthesis and their applications. In this review represented different methods of synthesis, reactivity and various biological activities of quinoxaline derivatives.Keywords: Quinoxaline, reactivity, biological activities, synthetic methods. IntroductionQuinoxaline and its derivatives are important nitrogen containing heterocyclic compounds of various biologically properties. Quinoxaline and its derivatives are mostly of synthetic origin. Substituted quinoxalines are an important class of benzoheterocycles, which constitute the building blocks of wide range of pharmacologically active compounds having antibacterial [1][2][3][4] [15] activities. The quinoxaline is described as a bioisoster of quinoline, naphthalene, benzothiophene and other aromatic rings such as pyridine and pyrazine. Because of the similarity between some antitubercular drugs and quinoxaline, as well as the presence of the quinoxaline moiety in some broad spectrum antibiotics, it was hoped that quinoxaline analogs would exhibit antitubercular activity [16]. The quinoxaline antibiotics are agents of bicyclic desipeptide antibiotic that have been reported activity against gram-positive bacteria and certain tumors and to inhibit RNA synthesis [17]. Quinoxaline has also been used in reactive dyes and pigments, azo dyes, fluroscein dyes and it also forms a part of certain antibiotics. Quinoxaline m.p. 29-30ºC and is miscible with water. It is weakly basic (pka 0.56) and thus considerably weaker base than the isomeric diazonapthalenes namely cinnoline (pka 2.42), pthalizine (pka 3.47) or quinazoline (pka 1.95). 2-Hydroxy-but not 2-amino quinoxaline exist in tautomeric forms.

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Section: Synthesis Of Quinoxalinesmentioning

confidence: 99%

“…Similarly, the condensation of dehydroascorbic acid with ophenylenediamine, led to compound which turns into pyrazolylquinoxalinone in the presence of arylhydrazines [77].…”

Section: From Dehydroascorbic Acidmentioning

confidence: 99%

Synthetic Methods and Exploring Biological Potential of Various Substituted Quinoxalin-2-one Derivatives

2016

European Reviews of Chemical Research

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“…In particular quinoxaline scaffolds were found as a core unit in a number of biologically active compounds. These include anticancer [2,3], antibacterial [4], antiviral [5], anti-inflammatory [6], anti HIV [7,8] and antihelmintic activities [9]. Quinoxaline derivatives are also used in the development of novel organic dyes and organic semiconductors.…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Clean Synthesis of Thiophenyl Thiazole Depended Novel Triazolo[4,3-<i>a</i>]Quinoxaline Derivatives

Kathrotiya

Gami

Naliapara

2015

ILCPA

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ABSTRACT.A simple and efficient approach for the synthesis of thiophenyl thiazole based triazolo [4,3-a]quinoxaline derivatives is described. In this methodology, 3-hydrazinyl-N-(4-(thiophen-2-yl)thiazol-2-yl)quinoxalin-2-amine derivatives treated with various aromatic aldehyde to form Schiff base which on treatment with iodobenzene diacetate in dichloromethane at room temperature to furnish title compounds. The synthesized compounds were characterized by 1 H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data. INTRODUCTION1,2,4-triazoles are very interesting targets for medicinal and pharmaceutical applications. The recent literatures are enriched with progressive findings about the synthesis and pharmacological action of fused heterocyclic systems. The structural diversity and biological importance of nitrogen containing heterocyclic systems have made them attractive synthetic targets over many years and they are found in various natural products [1]. Quinoxalines are an important class of nitrogen containing heterocycles with a variety of biological activities. In particular quinoxaline scaffolds were found as a core unit in a number of biologically active compounds. These include anticancer [2,3], antibacterial [4], antiviral [5], anti-inflammatory [6], anti HIV [7,8] and antihelmintic activities [9]. Quinoxaline derivatives are also used in the development of novel organic dyes and organic semiconductors. Triazolo [4,3-a]quinoxaline [10] have been reported to possess antiviral, and antimicrobial activities. Many other triazolo quinoxaline derivatives have been reported [11][12][13] to possess other types of biological properties. Thus, triazolo quinoxaline derivatives continue to attract much attention as these molecules are of potential biological interest.For synthesis purpose, triazolo quinoxalines can be achieved in several ways. Reaction of 1-(2-chloroquinoxalin-3-yl)hydrazine and triethyl orthoformate gave triazolo quinoxaline [14]. Reactions of benzyl bromide or benzyl cinnamate with N-(benzotriazol-1-ylmethyl)arylimidoyl chlorides in the presence of t-BuOK occur with opening of the benzotriazole ring affording 1,2,4-triazolo[1,5-a]quinoxalines [15]. Reaction of N'-(1,2-dihydro-2-oxoquinoxalin-3-yl)benzohydrazide and HMPA formed triazolo quinoxaline [16]. By heating 2-hydrazino 3-phenylquinoxaline with phenyl-1,3-butanedione produced triazolo quinoxaline [17]. N-(2-chloro-4a,8a-dihydroquinoline3yl-methyl)-N-3-chloro-quinoxalin-2yl) hydrazones cyclised by iodobenzene diacetate under microwave irradiation technique to furnish the respective quinolinyl-1, 2, 4-s-triazolo [4,3-a]quinoxalines [18]. Here we report an efficient and clean synthesis of thiophene thiazole depended novel triazolo quinoxaline derivatives by cyclisation reaction. The constitutions of all the products were confirmed using 1 H NMR, 13C NMR, FTIR, and elemental analysis. EXPERIMENTALRequired all reagents were obtained commercially. Solvents were purified and dried before being used. All melting points were taken in open ...

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“…In particular, quinoxalines were found as core units in a number of biologically active compounds. These include anticancer 2,3 antibacterial 4 , antiviral 5 , anti-inflammatory 6 , anti HIV 7, 8 , and antihelmintic activities 9 . Antioxidant compounds play an important role as a health-protecting factor.…”

Section: Introductionmentioning

confidence: 99%

In vitro antioxidant potential study of some synthetic quinoxalines

Hossain

et al. 2012

Bangladesh Med Res Counc Bull

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In continuation of our study the in vitro antioxidant activity of some novel quinoxaline derivatives was investigated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method with respect to ascorbic acid. To determine the antioxidant activity, a number of substituted indoxyls (3A-G), cyclic ketones (2A-G), and quinoxalines (1A-G) were synthesized by both microwave and conventional heating methods. The present findings revealed that some quinoxalines and their precursors (1D, 1F, 1G and 2E) exhibited a marked scavenging effect on DPPH radical.

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Synthesis of potential chemotherapic quinoxalinone derivatives by biocatalysis or microwave-assisted Hinsberg reaction

Cited by 70 publications

References 10 publications

Synthetic Methods and Exploring Biological Potential of Various Substituted Quinoxalin-2-one Derivatives

Synthetic Methods and Exploring Biological Potential of Various Substituted Quinoxalin-2-one Derivatives

An Efficient and Clean Synthesis of Thiophenyl Thiazole Depended Novel Triazolo[4,3-<i>a</i>]Quinoxaline Derivatives

In vitro antioxidant potential study of some synthetic quinoxalines

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