Simple and efficient synthetic procedures for the preparation of quinoxaline, pyrazine, pyridopyrazine, and benzoxazin2one derivatives were developed. Quinoxalines, also named as benzopyrazines, having a nitrogen ring, in organic chemistry is a hetrocyclic compounds containing a ring complex made up of a benzene ring and a pyrazine ring. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. The good inhibitory effect of quinoxaline derivatives 1517 has incited us to test 1,4dihydroquinoxaline2,3dione. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals, and antibiotics such as olaquindox, carbadox, echinomycin, levomycin and actinoleutin. Quinoxaline quinoxaline derivatives biological activity therapeutic application biomedical applications abstract quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. Discovery of quinazolinone and quinoxaline derivatives as. Sd1 and sd2 composed of electrondonating d moieties both in vertical and horizontal directions to an electronaccepting a quinoxaline at the central position have been synthesized. Therefore, the aim of this project was to synthesis some novel of 2,3substitutedquinoxaline. Lakhrissi 1 1 laboratory agroresources, polymers and process engineering, faculty of sciences. The cdk15 inhibitor, also referenced under cas 40254908, controls the biological activity of cdk15.
Quinoxaline, mixed metal, mixed ligand, metal complexes. In this regard, a series of quinoxaline derivatives 117 was synthesized and biologically evaluated against cholinesterases ache and bche and as well as against. These derivatives can be used as active molecules in pharmaceuticals. Quinoxaline 1,4dioxide compounds and desoxycarbadox quinoxaline 1,4dioxide compounds are antimicrobial agents that are used as animal growth promoters for livestock. Jul 30, 2010 many researchers have reported the synthesis and biological activity of quinoxaline derivatives 11,12,14. Quinoxaline pvc oled optoelectronic show properties solvatochromism a b s t r a c t two multifunctional quinoxaline containing small molecules designated as. Synthesis of quinoxaline derivatives 125 started with treating quinoxaline2carbohydrazide i.
Currents activated by kainate or rsalphaamino3hydroxy5methyl4isoxazolepropionic acid ampa in xenopus oocytes were inhibited competitively by. Synthesis and biological activities of some quinoxaline. A rapid, efficient, and reliable catalystfree procedure for the synthesis of quinoxaline derivatives in glycerol under focused microwave irradiation was developed. Cinnamil and quinoxalinederivative indicator dyes for. Quinoxaline 2, 3dione obtained from cyclocondensation reaction of ophenylene diamine with oxalic acid was reacted with three different ketones and formaldehyde to give the corresponding mannich bases in satisfactory yield. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. The new synthesis of quinoxaline derivatives monomer.
Microwaveassisted synthesis of quinoxaline derivatives using. An efficient protocol for the synthesis of quinoxaline. These contracts are legally binding agreements, made on trading screen of stock exchange, to buy or sell an asset in. Apart from their photophysical properties, the quinoxaline ring, composed of a benzene ring and a pyrazine ring, is a key moiety that confers various bioactivities. Proceeding from 2aminoquinoxaline3carbonitrile 1,4dioxides new derivatives of quinoxaline and quinoxaline 1,4dioxide were synthesized containing in the position 3 of the quinoxaline fragment 1,2,4oxadiazole and tetrazole rings. Synthesis of quinoxaline derivatives from terminal alkynes.
In general, the in vitro activity is significantly affected by substituents on the quinoxaline nucleus. Quinoxaline1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. As part of our ongoing research on the development of alternative synthetic procedures for the synthesis of biologically active heterocyclic compounds and the use of green chemistry techniques in organic synthesis, herein we report a simple and efficient method for the preparation of quinoxaline derivatives using heteropolyacids hpmo 11 vfeo 40. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. Jnk activation is achieved through activation of upstream kinases mkk4 andor mkk7 by jsp1. Pdf eight quinoxalinone derivatives were synthesized and investigated for. Pdf design and synthesis of some new quinoxalinebased. The metal complexes of quinoxaline derivatives are important due to their photochemical, photophysical, catalytic and biological properties. Their structures were confirmed by using 1 h nmr, ir, and mass analysis. Cn1966500a quinoxaline derivative, preparation method and. The inhibiting effect of some quinoxaline derivative. Quinoxalines are popular acceptor units applied in both opvs and oleds. Design, synthesis and antimicrobial activity of amide.
Synthesis and biological evaluation of new quinoxaline. Quinoxalines also called 1,4diazanaphthalenes or benzopyrines are bicyclic heterocycles containing a benzene ring fused to a pyrazine ring. Quinoxalines with amide and sulphonamide moieties have been reported to inhibit the growth of human tumor cell lines 8. Synthesis and antimicrobial activity of some new quinoxaline derivatives subba rami reddy sr, suryanarayana rao. The hydroxyl group was readily converted into a thiol function by treatment with phosphorus pentasulfide andor lawessons reagent in pyridine, and the subsequent. Pdf anticancer effect of a quinoxaline derivative gk. Pdf role of quinolones and quinoxaline derivatives in. Synthesis, reactions and biological activity of quinoxaline. Synthesis and neuropharmacological evaluation of some novel.
Therefore, inhibiting the activity of bche may be an effective way to control ad associated disorders. A series of substituted hydrazone and quinoxaline derivatives have been synthesized by appropriate methods. Biological activities of quinoxaline derivatives a antitubercular activity. Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles. All the compounds have been screened for their antibacterial activity againststaphylococcus aureusand escherichia coli. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinoxalines. Exploration of quinoxaline derivatives as antimicrobial. Heravi et al oiodoxybenzoic acid ibx, a readily available hypervalent iodine v reagent, was found to be highly effective in synthesis of quinoxaline derivatives, from 1,2diketones and ophenylenediamines at room. Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. The inhibitory potencies at excitatory amino acid eaa receptors of 11 quinoxaline derivatives were evaluated in twoelectrode voltageclamp recordings of xenopus oocytes injected with rat cortex mrna. Quinoxaline derivatives are widely distributed in nature and many of them, such as the antibiotics, levomycin and actinomycin possess very useful biological activity. Design of the synthesized compounds ixa,b, xviiia,b, viii a e, xvii a f and xxv. Multifunctional quinoxaline containing small molecules.
Derivatives of 1 are widely used as bridging ligand in both homobimetallic and heterobimetallic complexes. They can be formed by condensing orthodiamines with 1,2diketones. It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. Using in vitro cell cultures, we evaluated the influence of quinoxaline1,4dioxide, 2methylquinoxaline. In recent years, efforts are made to improve the synthesis of different quinoxaline derivatives with slight modi.
Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. Food and drug administration fda since 1998 for the control of swine dysentery. The sar results of quinoxaline derivatives are outlined in table 2. Two classes of quinazolinone derivatives and quinoxaline derivatives were identified as potent and selective polyadpribose polymerase1 and 2 parp1 and parp2 inhibitors, respectively. The catalyst is recyclable and reusable 2006 published by elsevier b. It is rare in natural state, but their synthesis is. Thus, the development of environmentally friendly benign green chemistry, highyielding and clean approaches for the synthesis of quinoxaline derivatives is still remains a highly desired goal in organic synthesis. Recent development of quinoxaline based polymerssmall.
Mamedov synthesis, reactions, mechanisms and structure. Onepot and efficient protocol for synthesis of quinoxaline. In pharmacological evaluation, the synthesized compounds showed its curative effect. The molecular targets of quinoxaline derivatives, which is a step. Study on the properties of the pvasf blend membranes p. To modify in their nucleus, they form different derivatives of quinoxaline which contains antimicrobial activity. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. Synthesis and characterization of new quinoxaline derivatives of 8hydroxyquinoline as corrosion inhibitors for mild steel in 1. Synthesis of new quinoxaline derivatives springerlink. Role of quinolones and quinoxaline derivatives in the advancement of treatment of tuberculosis article pdf available december 2015 with 193 reads how we measure reads. Twentynine new 67substituted quinoxaline 2carboxylate 1,4dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. Acceptor narrowbandgap polymers and their cyclized derivatives for bulkheterojunction polymer solar cell applications.
It is a colorless oil that melts just above room temperature. Many of the substituted quinoxaline compounds have been recently studied in considerable detail as effective corrosion inhibitors for steel and copper in acidic media 914. Quinoline and its fused heterocyclic derivatives tested with diverse pharmacological activity functional groups constitute an important class of compounds for new drug development. Quinoxaline1,4dioxide derivatives inhibitory action in. Quinoxaline derivatives exhibit a broad spectrum of biological activity such as antibacterial24, antifungal5,6, antiviral 7, anticancer8, antitubercular9, antimalarial10 and antiinflammatory11. Quinoxaline medical definition merriamwebster medical. Its molecular formula is c8h6n2, formed by the fusion of two aromatic rings, benzene and pyrazine. Therefore, the aim of this project was to synthesis some novel of 2,3substituted quinoxaline. It is proved that the compounds has jsp1 inhibition through biological test. Highly efficient synthesis of quinoxaline derivatives from. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. Thus, a series of 18 such derivatives have been synthesized, characterized on the basis of spectroscopic method and were tested for their antimicrobial activity against staphylococcus aureus staph.
Design and synthesis of new quinoxaline derivatives as. Oacetyl salicyloyl chloride and aromatic sulfonyl chloride derivatives. Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2. Quinoxaline derivatives of severalalkaloids springerlink. A few quinoline derivatives 42 developed by manera et al. In the light of these facts we decided to synthesize some new quinoxaline derivatives incorporating aromatic aldehyde and aromatic amine moieties attached to a 2hydroxy3methylquinoxaline nucleus with an ether linkage followed by the. Mar 26, 2010 new quinoxaline derivatives were prepared by reaction of 2quinoxalinehydroximoylbromide with the alkaloids anabasine, cytisine, and salsoline. Predicted data is generated using the us environmental protection agencys episuite. Synthesis and antimicrobial activities of some novel. Unusual ways of jnk are related with many pathological processes of diseases, for example. Synthesis of thymidine phosphorylase inhibitor based on. Anticancer effect of a quinoxaline derivative gk as a transglutaminase 2 inhibitor article pdf available in journal of cancer research and clinical oncology 98 april 20 with 372 reads. Pdf quinoxalinebased semiconducting materials are currently of high interest in the field of organic photovoltaics. Bioinspired orthoquinone catalysts have been applied to oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.
Compared with the standard icf01012, all the newly synthesized quinoxaline derivatives 125 i1ag displayed a strong affinity for synthetic melanin in water table 1. In attempt to develop new potent antitumor agents, a series of quinoxaline derivatives was designed and synthesized. Quinoxaline definition of quinoxaline by the free dictionary. Synthesis and antimicrobial activity of some new quinoxaline. Quinoxaline derivatives are widely distributed in nature and. Mar 12, 2012 as part of our ongoing research on the development of alternative synthetic procedures for the synthesis of biologically active heterocyclic compounds and the use of green chemistry techniques in organic synthesis, herein we report a simple and efficient method for the preparation of quinoxaline derivatives using heteropolyacids hpmo 11 vfeo 40.
Synthesis and biological evaluation of new quinoxaline derivatives. Pdf role of quinolones and quinoxaline derivatives in the. Quinoxaline is a bicyclic aromatic system with a benzene ring fused to a pyrazine ring. Quinoxaline1,4dioxide derivatives are synthetic heterocyclic compounds with multiple biological and pharmacological effects. Thus, quinoxaline derivatives have been reported application as dyes. Several quinoxaline derivatives are also known to have strong antitumor activity. The invention discloses quinoxaline derivatives or salts thereof having pde9inhibiting activity and being useful as treating agent of dysuria and the like, which are represented by the formula i in the formula, r 1 and r 2 each independently stands for hydrogen, halogen, alkyl, alkoxy, acyl, amino and the like, r 3 stands for alkyl, aryl, saturated carbocyclic group, saturated. It is rare in natural state, but their synthesis is easy to perform. The complexes of quinoxaline with several metal ions have been. Lproline as an e cient organocatalyst for the synthesis of. Exploring biological activities of quinoxaline derivatives. Quinoxaline and arylaminoalcohol derivatives as antiplasmodial. A previous docking study with different quinoxaline derivatives demonstrated a strong interaction with the poly adpribose polymerase of t. Herein, we report a green and e cient method for the synthesis of quinoxaline derivatives in high yields and short reaction times by the condensation of 1,2diamines with 1,2dicarbonyl compounds.
The first example of quinoxaline as a unit in conductive polymers was reported in 1993 1993mm3464. Kiran ga, laxminarayana eb, thirumala chary mc and ravinder ma. Quinoxaline 1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. The reaction proceeded through initial program aiming at merging of quinoxaline, azole. Facile synthesis of quinoxaline derivatives using o. Its molecular formula is c 8h 6n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Galliumiii triflatecatalyzed synthesis of quinoxaline derivatives article in tetrahedron letters 4952. The novel compounds were tested in vitro for their antiproliferative activities against hepg2, mcf7 and hct116 cell lines. Galliumiii triflatecatalyzed synthesis of quinoxaline. Pdf synthesis and neuropharmacological activity of some. Very recently we have developed a convenient and efficient procedure for synthesis of quinoxaline derivatives using cupric sulfate pentahydrate as catalyst. Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. They are wellknown for application in organic light emitting devices, polymers and pharmaceutical agents. Synthesis of new quinoxaline2carboxylate 1,4dioxide.
Some of these compounds have been screened for antiinflammatory activity against the carageenan. Quinoxalines and fused ring systems show diverse pharmacological activities. Furthermore, methoxy quinoxaline derivatives 3c and quinoxaline derivatives bearing substituted pyridines 6a,b, 12a,b, and a,b were designed to. Quinoxaline derivatives are important components of pharmacologically active compounds, including antibacterial, antibiotic, and antitumor agents, antifungal, antiinflammatory, and analgesic activities, as well as use in rna. The activity of these inhibitors against parp2 is about 10fold more potent than against parp1. In this study, we investigated the bioactivity of five quinoxaline1,4dinoxides derivatives in different animal cell lines. The synthesized compounds were characterized by ir, 1h nmr, c nmr and mass spectra, and. The complexes of quinoxaline with several metal ions have been studied by various workers. Discovery of quinazolinone and quinoxaline derivatives as potent and selective polyadpribose polymerase12 inhibitors akinori iwashitaa, kouji hattorib, hirofumi yamamotob, junya ishidab, yoshiyuki kidob. A quinoxaline derivative as a potent chemotherapeutic. Quinoxalines heterocyclic building blocks sigmaaldrich. In parp enzyme assays using recombinant parp1 and parp2, quinazolinone derivatives displayed relatively high selectivity for parp1 and quinoxaline.
The quinoxalinecontaining polymers are applicable in optical devices due to their thermal stability and low band gap. Quinoxaline synonyms, quinoxaline pronunciation, quinoxaline translation, english dictionary definition of quinoxaline. Cn1966500a quinoxaline derivative, preparation method. Seven quinoxaline carboxamide derivatives were synthesized and radiolabeled with iodine125. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines hct116 human colon. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Efficient synthesis of quinoxaline derivatives catalyzed. Synthesis of quinoxaline derivatives catalyzed by lproline. In ongoing work to design quinoxaline derivatives for tumortargeted melanoma chemotherapy, the first challenge was to maintain a high affinity for melanin. Abstract new quinoxaline derivatives were prepared by the reaction of 2hydroxyquinoxaline 1 and alkyl or alkylaminoalkyl halides in dimethylformamide using potassium carbonate as a base. Compared with the classical synthetic method, this new method has the advantages of convenient manipulation and environmental.
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