Twentynine new 67substituted quinoxaline2carboxylate 1,4dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. Synthesis of quinoxaline derivatives by catalytic strategies. The reaction proceeds with operational simplicity, an easily available catalyst system, and. Accordingly, a series of novel quinoxaline derivatives were synthesized and evaluated theirs in vitro and in vivo activity against cmet kinase. Request pdf synthesis of new quinoxaline derivatives proceeding from 2aminoquinoxaline3carbonitrile 1,4dioxides new derivatives of quinoxaline and quinoxaline 1,4dioxide were synthesized.
It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines hct116 human colon. Direct synthesis of novel quinoxaline derivatives via. Technology development centre, custom pharmaceutical services, dr. Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles. In pharmacological evaluation, the synthesized compounds showed its curative effect against. A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against m.
It has been observed that the presence of a chloro, methyl, or methoxy group in position 7 of the benzene moiety reduces the mic and ic50. Pdf new quinoxaline derivatives as potential mt1 and mt2. Quinoxaline antibiotic is a generic name given to a family of heterodetic cyclodepsipeptide antibiotics which contain a quinoxaline moiety in the molecule kuroya et al. The importance of quinoxaline derivatives comes from its nitrogen contents heterocyclic compounds.
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 na2pdp2o7 as a new highly efficient bifunctionalheterogeneous catalyst. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. Gabaabenzodiazepine receptor, quinoxaline and quinazoline derivatives, mtd, mlr. Pdf quinoxaline moieties are nitrogen containing heterocyclic derivatives which have broad spectrum. Quinoxaline derivative an overview sciencedirect topics. Functionalized metallonanobelt derivatives having quinoxaline scaffold prepared from a common precursor. Synthesis of new quinoxaline2carboxylate 1,4dioxide. Here, a palladiumcatalyzed new hydrogenative annulation reaction of catechols and nitroarylamines, allowing straightforward access to two classes of novel quinoxaline derivatives, is reported. Quinoxaline derivatives are an important class of heterocyclic compounds, in which n replaces one or more carbon atoms. Quinoxaline2carbonitrile derivatives has good antimycobacterial activity but appeared to be quite toxic ortega et al.
Ramona rad, maria mracec, mircea mracec and tudor oprea. Efficient assembly of quinoxaline derivatives from benzene1,2. Many researchers have reported the synthesis and biological activity of quinoxaline derivatives 11,12,14. Novel and selective butyrylcholinesterase inhibitors volume. A green protocol for the synthesis of quinoxaline derivatives. Unlimited viewing of the articlechapter pdf and any associated.
Ecofriendly approach to access of quinoxaline derivatives. Quinoxaline derivatives are an important class of heterocyclic compounds, in which n replaces one or more carbon atoms of the naphthalene ring. Synthesis and antimicrobial activities of some novel. Tb activities and might be able to prevent the drug resistance to a certain extent. Compounds 3a3i were obtained by the condensation of o phenylenediamines with 1,2. Aurang zeb, abdul hameed, latifullah khan, imran khan, kourosh dalvandi, m. Ecofriendly approach to access of quinoxaline derivatives using. Wed like to understand how you use our websites in order to improve them. Although quinoxaline itself is mainly of academic interest, quinoxaline. Synthesis and reactions of quinoxalines dyuthi cusat. Tpzs are synthesized from glyoxal and 3,4diaminothiophene 1983bsf159. The quinoxaline derivatives are more hydrophobic than aa and dhaa, and it is possible to obtain a reversedphase hplc method with a high efficiency, selectivity, and baseline separation of the two quinoxaline derivatives corresponding to aadhaa and iaadhiaa. Since quinoxaline derivatives are regarded as a new class of effective anti.
There are a wide range of quinoxaline derivatives with antimicrobial activity documented. The quinoxaline derivatives are used for the cure of vast range of various diseases. 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. These colorless antibiotics are derived from various species of streptomycetes and are highly active against grampositive bacteria. Vidyasagar 3 1suresh gyan vihar universe, jaipur, rajsthan. 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. 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. Mohammad badali1,2, jabbar khalafy1, masomeh aghazadeh3. Due to a larger quinoidal character, the band gap of tpzcontaining polymers is smaller than that of the quinoxaline containing derivatives 2008mm6012. The outputs and descriptors calculated by the monte carlo simulation, such as the total adsorption.
Furthermore, methoxy quinoxaline derivatives 3c and quinoxaline derivatives bearing substituted pyridines 6a,b, 12a,b, and a,b were designed to be synthesized. Quinoxaline derivatives are of significant interest as they are noteworthy. 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. An efficient protocol for the synthesis of quinoxaline. Their structures were confirmed by using 1 h nmr, ir, and mass analysis. Quinoxaline nucleus based derivatives have attracted researchers attention due to privileged and extensive applications in medicine, pharmaceuticals and. The privilege structures hypothesis for g proteincoupled receptors some preliminary results. New quinoxaline derivatives as potential mt1 and mt2. Exploration of quinoxaline derivatives as antimicrobial.
It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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. Quinoxaline1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. Chromophorelabeled quinoxaline derivatives as efficient. The structure of quinoxaline derivatives were confirmed by using ir, 1hnmr, mass spectroscopy. Synthesis and biological evaluation of quinoxaline. Research institute of chemistry, international center for chemical and biological sciences, university of karachi, karachi75270, pakistan. Quinoxaline 1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine.
Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. Are molecular 5,8extended quinoxaline derivatives good. Introduction quinoxaline derivatives have different pharamacological activities such as bacteriocides and insecticides 1, antibacterial 25, antifungal 2, 6, antitubercular 2, 79, 10, analgesic 4, 11 and antiinflammatory 11, 12. A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. The hydroxyl group was readily converted into a thiol function by treatment with phosphorus pentasulfide andor lawessons reagent in pyridine, and the subsequent alkylation of the thiol group was carried out. They are important in industry due to their ability to inhibit the metal corrosion,, in the preparation of the porphyrins, since. Quinoxaline derivatives as corrosion inhibitors of carbon. The 4acetoxybenzyl ester of pyrazinoic acid and 4acetoxybenzyl 2quinoxalinecarboxylate showed excellent activity against mtb mic ranges of less than 1. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the.
The approved location for the quinoxaline ring system is shown in fig. Pdf new opportunities for the synthesis of quinoxaline. A convenient process of preparing of 2,3 diphenyl quinoxaline derivatives. It is a colorless oil that melts just above room temperature.
Substituted quinoxaline diketones 7 can be prepared by oxidation of alkynes 6 with. Design and synthesis of new quinoxaline derivatives as. Facile synthesis of quinoxaline derivatives using o. Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible. Pdf a convenient process of preparing of 2,3 diphenyl. An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using recyclable aluminasupported heteropolyoxometalates diego m. The complexes of quinoxaline with several metal ions have been studied by various workers. Design of novel quinoxaline scaffold as cmet kinase inhibitor. Twentynine new 67substituted quinoxaline 2carboxylate 1,4dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. Quinoxaline derivatives exhibit a broad spectrum of biological activity such as antibacterial24, antifungal5,6, antiviral 7, anticancer8, antitubercular9, antimalarial10 and antiinflammatory11.
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. Ever since the idea arose that melatonin might promote sleep and resynchronize circadian rhythms, many research groups have centered their efforts on obtaining new melatonin receptor ligands whose pharmacophores include an aliphatic chain of variable length united to an nalkylamide and a methoxy group or a bioisostere, linked to a central ring. Prepared quinoxaline derivatives were also tested for their antioxidant activity by the. Author links open overlay panel yoko sakata a b yoshiki furukawa a shigehisa akine a b. Volume 60, issue 31, 1 august 2019, pages 20492053. Synthesis and antimycobacterial activity of pyrazine and. Download fulltext pdf download fulltext pdf new quinoxaline derivatives as potential mt1 and mt2 receptor ligands article pdf available in molecules 177. Quinoxaline derivatives are widely distributed in nature and many of them, such as the antibiotics, levomycin and actinomycin possess very useful biological activity. Therefore, the aim of this project was to synthesis some novel of 2,3substitutedquinoxaline. In general, the in vitro activity is significantly affected by substituents on the quinoxaline nucleus. Novel rearrangement of certain quinoxaline noxides to 6benzimidazolinones. Chromophores were embedded both at quinoxaline and triarylamine units, and their influence on photophysical and thermal properties was investigated. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4.
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