The number of structural variations employed has been, however, quite limited to date. They can be formed by condensing orthodiamines with 1,2diketones. It is a colorless oil that melts just above room temperature. Shibi e a department of chemistry, vidya bharati college, camp, amravati, maharashtra, india. 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. To describe the binding affinity of ampa receptor, all experimental values for the inhibition constant k i given in literature was converted to pk i.
Facile route for the synthesis and characterization of new. Naphtho quinoxaline, anthraptereidine, anthrapyridine, triazolopetridine, anthrapyridine, triazolopyridine derivatives were synthesized from 2aminoanthraquinone and 3amino2cyanonaphtho2,3 f quinoxaline 7,12dione 4 and based on different reactive sites a series of new derivatives were prepared. Convenient and simple procedures for the synthesis of phenazine and quinoxaline derivatives were developed via a reaction of ophenylenediamines and 1,2dicarbonyl compounds. 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. In addition, the synthesis of two new 1,4benzodiazine derivatives and the. Dec 16, 20 a new onepot protocol has been developed for the synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine4carboxylates with benzene1,2diamines, ethane1,2diamine, and 2aminophenols in the presence of biotf3 5 mol % under mild conditions in very good yields. Quinoxaline derivatives of severalalkaloids springerlink. Very recently we have developed a convenient and efficient procedure for synthesis of quinoxaline derivatives using cupric sulfate pentahydrate as catalyst. 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.
The present protocol opens a new way for cc, cn, and co bond. Steroidal oxazolo4,5b quinoxaline 2ylhydrazone derivatives 5ac were prepared by multistep synthesis 6. The complexes of quinoxaline with several metal ions have been. Design and syntheses of some new quinoxaline derivatives. How to merge pdfs and combine pdf files adobe acrobat dc. Synthesis and neuropharmacological evaluation of some novel. Compounds containing the quinoxaline nucleus exhibit a broad spectrum of biological activity such as antibacterial 1,2,3, antifungal 4,5, antiviral, anticancer, antituberculosis, antimalarial and antiinflammatory properties.
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. In pharmacological evaluation, the synthesized compounds showed its curative effect. In this report, we disclose a facile and efficient copper. Quinoxaline1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. The antibacterial activity of these compounds was evaluated by the disk diffusion assay against two grampositive and two.
Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. Quinoxaline derivatives are widely distributed in nature and many of them, such as the antibiotics, levomycin and actinomycin possess very useful biological activity. You can merge pdfs or a mix of pdf documents and other files. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Technology development centre, custom pharmaceutical services, dr. 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. By inducing sp2 natoms into the quinoxaline backbone, the electron a. The catalyst is recyclable and reusable 2006 published by elsevier b. Mohga mb, ashraf am, hanan mr, afaf a elm 2007 synthesis and antimicrobial activity of novel quinoxaline derivatives. Patil a, nilesh padole b, taibi ben hadda c, ahmed a. The question numbers have been retained for ease of comparison.
Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2. Therefore, the aim of this project was to synthesis some novel of 2,3substituted quinoxaline. Quinoxaline2, 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. Pondicherry university a central university directorate of distance education financial derivatives paper code. Molecules 2019, 24, 1175 3 of 22 is a wellknown diarylurea multitargeted inhibitor of several kinases including raf, vegfr, ckit and pdgfr 17. The complexes of quinoxaline with several metal ions have been studied by various workers. Quinoxalines and fused ring systems show diverse pharmacological activities. Turning on fluorescent emission from calkylation on. Fecl3catalyzed synthesis of pyrrolo1,2aquinoxaline.
Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles. Synthesis and biological activities of some quinoxaline. A series of substituted hydrazone and quinoxaline derivatives have been synthesized by appropriate methods. Dna and protein interacting scaffold for pharmacological activities. 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. Quinoxaline derivatives exhibit a broad spectrum of biological activity such as antibacterial24, antifungal5,6, antiviral 7, anticancer8, antitubercular9, antimalarial10 and antiinflammatory11. Design, synthesis, optoelectrochemical and theoretical investigation of novel indolo2, 3. Pyrrolo3,2 bquinoxaline derivatives as types i and ii eph.
Based on pyrazole derivatives showing egfr tyrosine kinase inhibitory activity 59,60 and on the potential of quinoxaline derivatives as anticancer candidates,, a series of 3,3a,4,5tetrahydro2hbenzogindazole containing quinoxaline derivatives was synthesized. The present protocol opens a new way for cc, cn, and co bondformation. Click, drag, and drop to reorder files or press delete to remove any content you dont want. The discovery of novel synthetic methodologies to facilitate the preparation of the compound libraries is a pivotal focal point of research activity in the field of modern medicinal and combinatorial chemistry.
A new onepot protocol has been developed for the synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine4carboxylates with benzene1,2diamines, ethane1,2diamine, and 2aminophenols in the presence of biotf3 5 mol % under mild conditions in very good yields. Therefore, inhibiting the activity of bche may be an effective way to control ad associated disorders. A series of nheterocyclic quinoxaline derivatives was successfully synthesized and applied as hole transport layers in quantum dot lightemitting diodes qleds. Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. These questions and solutions are based on the readings from mcdonald and are identical to questions from the former set of sample questions for exam mfe. Such a structural change resulted in interrupted cyclicring systems with electrondonating amine sp3type and electronaccepting imine sp2type units bridged by a phenylene unit. In pharmacological evaluation, the synthesized compounds showed its curative effect against. Based on the abovementioned antiproliferative quinoxaline compounds 15 and sorafenib as a urea derivative 18, we aimed to design a new series of quinoxaline based compounds with amide.
Synthesis of highly functionalized polycyclic quinoxaline. An efficient protocol for the synthesis of quinoxaline. This work is licensed under a creative commons attributionnoncommercial 3. Molecular docking and 3d qsar studies of quinoxaline. Therefore, the aim of this project was to synthesis some novel of 2,3substitutedquinoxaline. New quinoxaline derivatives were prepared by reaction of 2quinoxalinehydroximoylbromide with the alkaloids anabasine, cytisine, and salsoline. In this paper we report on the synthesis of a series of quinoxaline monomers and. Isatin derivatives, quinoxaline derivatives, ophenylenediamine, microwave irradiation. A straightforward fecatalyzed method for the synthesis of pyrrolo1,2aquinoxalines from 12aminophenylpyrroles and cyclic ethers, which includes functionalization of csp3h bonds and the construction of cc and cn bonds, has been developed. Progress in quinoxaline synthesis part 2 request pdf.
Compound 1 was prepared according to previously reported procedures by condensation of commercially available 2,3dichloroquinoxaline with malononitrile in the presence of sodium hydride. Derivatives in the present study, addition of nitroso group at position 1 of 2aminoanthraquinone 1 to yield 2amino1nitroanthraquinone 2 was carried out by the reaction of compound 1 with sodium nitrite in water. Chlorides and iodides are more active towards bacteria than fungi. In silico investigation of the structural requirements for. Quinoxaline derivatives with broadened absorption patterns. The xray crystal structures of the catalytic domain of the epha3 tyrosine kinase in complex with two type i inhibitors previously discovered in silico compounds a and b were used to design type i12 and ii inhibitors. Their structures were confirmed by using 1 h nmr, ir, and mass analysis. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. Compound 2 was used as starting material to produce many new naphtho2,3f quinoxaline. Facile synthesis of quinoxaline derivatives using o.
A combined experimental and computational study showing 14 of 8 pages in this article. All the compounds have been screened for their antibacterial activity againststaphylococcus aureusand escherichia coli. These derivatives were prepared via the reaction of steroidal semicarbazones with 2,3dichloroquinoxaline. Quinoxalinebased semiconducting materials are currently of high interest in the field of organic photovoltaics. Steroidal oxazolo4,5bquinoxaline2ylhydrazone derivatives 5ac were prepared by multistep synthesis 6. Synthesis, reactions and biological activity of quinoxaline. Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible. A quinoxaline based nheteroacene interfacial layer for. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. Recent trends in synthesis of quinoxaline and its derivatives. Many researchers have reported the synthesis and biological activity of quinoxaline derivatives 11,12,14. Theoretical approach to the corrosion inhibition ef. Thermodynamic properties of quinoxaline1,4dioxide derivatives.
A novel approach for cc, cn, and co bond formation. Click add files and select the files you want to include in your pdf. Unlimited viewing of the articlechapter pdf and any associated supplements and figures. In this paper we report on the synthesis of a series of quinoxaline monomers and triads with improved optical. Acceptor narrowbandgap polymers and their cyclized derivatives for bulkheterojunction polymer solar cell applications. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. 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.
In this regard, a series of quinoxaline derivatives 117 was synthesized and biologically evaluated against cholinesterases ache and bche and as well as against. Pdf a facile synthesis of phenazine and quinoxaline new. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. The xray crystal structures of the catalytic domain of the epha3 tyrosine kinase in complex with two type i inhibitors previously discovered in silico compounds a and b were used to design type i12 and ii. Jul 30, 2010 many researchers have reported the synthesis and biological activity of quinoxaline derivatives 11,12,14.
It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. Synthesis and antimicrobial activities of some novel. For more information, read michigan publishings access and usage policy. Quinoxaline 1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine.
Onepot and efficient protocol for synthesis of quinoxaline. Design and syntheses of some new quinoxaline derivatives containing pyrazoline residue as potential antimicrobial agents. 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. Naphthoquinoxaline, anthraptereidine, anthrapyridine, triazolopetridine, anthrapyridine, triazolopyridine derivatives were synthesized from 2aminoanthraquinone and 3amino2cyanonaphtho2,3 fquinoxaline7,12dione 4 and based on different reactive sites a series of new derivatives were prepared. Synthesis and antimicrobial activity of some new quinoxaline. Some of these compounds have been screened for antiinflammatory activity against the carageenan. Pyrrolo3,2 bquinoxaline derivatives as types i and ii. Compounds 1 a and 1 b are strongly fluorescent in aprotic solvents while symmetrical derivatives 2 a and 2 b were non.