Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. This is a pdf file of an unedited manuscript that has been accepted for publication. Quinoxaline nucleus based derivatives have attracted researchers attention due to privileged and extensive applications in medicine, pharmaceuticals and. Quinoxaline1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. In the present study, we report the synthesis of various quinoxaline derivatives from direct condensation of substituted aromatic 1,2diamine. Synthesis, characterization, antibacterial and anti. Synthesis of bisquinoxaline derivatives using tonsil clay as a catalyst. Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. Such a structural change resulted in interrupted cyclicring systems with electrondonating amine sp3type and electronaccepting imine sp2type units bridged by a phenylene unit. Pdf green synthesis of quinoxaline derivatives researchgate. The series of 3methyl2phenylthioquinoxaline 1,4dinoxide derivatives. Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles.
Design and synthesis of new quinoxaline derivatives as anticancer. Ecofriendly approach to access of quinoxaline derivatives using. If you previously purchased this article, log in to readcube. Microwaveassisted synthesis of 5,6dihydroindolo1,2a. Quinoxaline derivatives as new inhibitors of coxsackievirus b5. Quinoxaline derivatives are known for their cancer chemopreventive effect. 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. A convenient and efficient synthesis of new bis quinoxaline is described, involving condensation of 1,2diamines with 9ethyl3,6di1,2dioxoethylcarbazole in the presence of tonsil clay, a readily available and inexpensive catalyst. Liposomebased nanocarrier loaded with a new quinoxaline.
The most common method relies on the condensation of. Quinoxaline derivatives are an important class of heterocyclic compounds, in which n replaces one or more carbon atoms. As shown in figure 4, zanettis team reported a series of 3methylquinoxaline 1,4dinoxide derivatives with a phenylthio, phenylsulfonyl, or phenylsulfinyl linked in r2 position of quinoxaline subunit figure 4a. The present experiment sought to determine whether treatment with these compounds produces changes in affective responses. New quinoxaline derivatives were tested against different rna and dna viruses. This method rapidly afforded the tetracyclic products with good to excellent yields 8397% in. Two new quinoxalinone derivatives have been synthesized adopting the hong method, and investigated for some neuropharmacological effects anxiety and depressivelike responses in rats. This growth has run in parallel with the increasing direct reliance of companies on the capital markets as the major source of longterm funding. Synthesis and influence of two quinoxalinone derivatives. General asymmetric hydrogenation of 2alkyl and 2aryl.
Under mild reaction conditions, the corresponding biologically relevant 2substituted1,2,3,4tetrahydroquinoxaline units were obtained in high yields and good to excellent enantioselectivities up to 95%. Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. A novel onepot synthesis of quinoxaline derivatives in. Pdf new opportunities for the synthesis of quinoxaline. The derivatives market helps to transfer risks from those who have them but may not like them to those who have an appetite for them. New quinoxaline derivatives were prepared by reaction of 2quinoxalinehydroximoylbromide with the alkaloids anabasine, cytisine, and salsoline. The complexes of quinoxaline with several metal ions have been. Their structures were characterized by ir, 1hnmr, cnmr, and ms spectra and elemental analyses. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines hct116 human colon.
Quinoxaline derivative an overview sciencedirect topics. Synthesis of quinoxaline derivatives catalyzed by lproline. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Quinoxaline derivatives of severalalkaloids, chemistry of. If the inline pdf is not rendering correctly, you can download the pdf file here. Catalyzed annulation synthesis of spiro pyrrolo1,2. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. This work is licensed under a creative commons attributionnoncommercial 3. Unit i financial derivatives introduction the past decade has witnessed an explosive growth in the use of financial derivatives by a wide range of corporate and financial institutions. Design and synthesis of novel quinoxaline derivatives as.
Facile synthesis of quinoxaline derivatives using o. General procedure for the preparation of oalkynyl carbonyl derivatives 1 and quinoxaline and phenazine derivatives and spectral data for selected compounds. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford. The outputs and descriptors calculated by the monte carlo simulation, such as the total adsorption. Quinoxaline derivatives are widely distributed in nature and many of them, such as the antibiotics, levomycin and actinomycin possess very useful biological activity. It is rare in natural state, but their synthesis is easy to perform. The first example of quinoxaline as a unit in conductive polymers was reported in 1993 1993mm3464. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. The catalyst is recyclable and reusable 2006 published by elsevier b. Read quinoxaline derivatives of severalalkaloids, chemistry of natural compounds on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. 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. Onepot threecomponent synthesis of quinoxaline and phenazine ring systems using fischer carbene complexes.
Download acrobat pdf file 498kb supplementary material. Results and discussion at first, ionic liquid 1,3disulfonic acid imidazolium chloride dsimcl was prepared. In the meantime, there were other research groups studying the antimycobacterial activity of qdnos. 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. All the new compounds were screened for their in vitro antiproliferative activities against three human cancer cell lines mcf7, smmc7721 and hela and noncancerous. Therefore, inhibiting the activity of bche may be an effective way to control ad associated disorders. A number of synthetic strategies have been developed for the preparation of substituted quinoxalines 2. Quinoxalines and fused ring systems show diverse pharmacological activities. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. Sensing study of quinoxaline analogues with theoretical.
In the present study, we report the synthesis of various quinoxaline derivatives from direct condensation of substituted aromatic 1,2diamine with 1,2dicarbonyl catalyzed by nanostructured pyrophosphate na 2 pdp 2 o 7 as a new highly efficient bifunctionalheterogeneous catalyst. Synthesis and evaluation of new quinoxaline derivatives of. These contracts are legally binding agreements, made on trading screen of stock exchange, to buy or sell an asset in. Quinoxaline derivatives as corrosion inhibitors of carbon. Article on thermodynamic properties of quinoxaline1,4dioxide derivatives and a combined experimental and computational study. Chemistry and pharmacological diversity of quinoxaline. Quinoxaline derivatives of severalalkaloids springerlink. Pdf the objective of present research work is to provide green technique for synthesis of 2,3diphenyl quinoxaline. The solvent hfip can be readily separated from reaction products and recovered in excellent purity for direct reuse. For more information, read michigan publishings access and usage policy. Very recently we have developed a convenient and efficient procedure for synthesis of quinoxaline derivatives using cupric sulfate pentahydrate as catalyst. Reduction on imine moiety cn of quinoxalines by alkylaryllithiums led to a geometrical change on the quinoxaline ring, thereby perturbing the electronic structure to turn on fluorescence emission.
Lproline as an e cient organocatalyst for the synthesis. In this regard, a series of quinoxaline derivatives 117 was synthesized and biologically evaluated against cholinesterases ache and bche and as well as against. 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. A series of quinoxaline derivatives were efficiently synthesized in excellent yields by the reaction of 1,2diamines and 1,2diketones with grinding. Turning on fluorescent emission from calkylation on. The high commercial demand for quinoxalines needs a rapid, greener and safer synthetic method among the chemists.
A facile and efficient method for the synthesis of quinoxaline derivatives using sulfooxy ethylsulfamic acid as a novel difunctional bronsted. We found that the chronic injection of 6nitro21hquinoxalinone nqu showed. A general asymmetric hydrogenation of a wide range of 2alkyl and 2arylsubstituted quinoxaline derivatives catalyzed by an iridiumdifluorphos complex has been developed. Synthesis of bisquinoxaline derivatives using tonsil clay. Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2. As a service to our customers we are providing this early version of the manuscript. Ferric chloride served as a promoter and as a lewis. Regarding the antiprotozoal activity, quinoxaline derivatives with different substitutions, 4substituted pyrrolo1,2aquinoxalines, 3phenyl1.
The objective of present research work is to provide green technique for synthesis of 2,3diphenyl quinoxaline. Enzymaticchemical preparation of quinoxaline derivatives. Synthesis, characterization, antibacterial and antifungal activities of new quinoxaline 1,4dinoxide derivatives abstract fulltext html download as pdf. Quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely. A series of quinoxaline derivatives has been synthesized by condensation of diamines and dicarboniles in microwave heating conditions and in solvent free media. Many researchers have reported the synthesis and biological activity of quinoxaline derivatives 11,12,14. Microwave assisted synthesis of some quinoxaline derivatives. It is a colorless oil that melts just above room temperature. A series of quinoxaline derivatives were efficiently synthesized in excellent yields by the reaction of 1,2diamines and 1,2diketones with grinding catalyzed by p. Onepot threecomponent synthesis of quinoxaline and. Hexafluoroisopropanol hfip is explored as an effective medium for the synthesis of quinoxaline derivatives in high yields at room temperature. Figure 10 represents the top and side views of the most suitable configuration for adsorption of quinoxaline derivatives on fe 1 1 0 substrates obtained by monte carlo simulation.
Quinoxaline derivatives exhibit a broad spectrum of biological activity such as antibacterial24, antifungal5,6, antiviral 7, anticancer8, antitubercular9, antimalarial10 and antiinflammatory11. Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. 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. Ecofriendly approach to access of quinoxaline derivatives. 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. Pdf anticancer effect of a quinoxaline derivative gk. Download fulltext pdf anticancer effect of a quinoxaline derivative gk as a transglutaminase 2 inhibitor article pdf available in journal of cancer research and clinical oncology 98.
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