The mechanism of action of the anti-herpes virus compound 2,3-dimethyl-6(2-dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline

Harmenberg, Johan; Åkesson-Johansson, Annelie; Gräslund, Astrid; Malmfors, Törbjorn; Bergman, Jan; Wahrén, Britta; Åkerfeldt, Stig; Leif, Lundblad,; Cox, Susan

doi:10.1016/0166-3542(91)90066-z

Cited by 83 publications

(39 citation statements)

References 17 publications

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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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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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“…Indolo [2,3-b]quinoxalines not only possess many important applications in material sciences, but also in medicinal chemistry. Earlier research showed that indolo [2,3-b]quinoxaline derivatives exhibit a wide range of interesting biological activities, such as antiviral [15,16] anticancer [17,18] antimicrobial [19] and antibacterial activities [20].…”

Section: Introductionmentioning

confidence: 99%

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

Shaikh¹,

Sharma²,

Kamble

2015

Can. Chem. Trans.

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Abstract:In this work, 5-methyl-5H-Benz[g]indolo [2,3-b]quinoxaline (BIQCH 3 ) and its derivatives were prepared in good yield by condensing 5-Substituted-1-methyl-1H-Indole-2,3-dione and 2,3-diaminonaphthalene in glacial acetic acid. The structure of BIQCH 3 and its derivatives were confirmed using FT−IR, 1 H NMR, 13 C NMR, Mass spectra and elemental analysis. The photophysical and electrochemical studies of BIQCH 3 and its derivatives were studied by UV-Visible spectroscopy, fluorescence spectroscopy and cyclic voltammetry respectively. The optical energy band gap of BIQCH 3 and its derivatives lies in the range of 2.53 ̶ 2.58 eV. Thermal analysis of BIQCH 3 and its derivative were studied by Thermo Gravimetric Analysis (TGA) and Differential Thermal Analysis (DTA).

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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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The mechanism of action of the anti-herpes virus compound 2,3-dimethyl-6(2-dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline

Cited by 83 publications

References 17 publications

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

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

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

In vitro antioxidant potential study of some synthetic quinoxalines

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