In pharmacological evaluation, the synthesized compounds showed its curative effect. The reaction proceeded in glycerol without any catalyst making this methodology valuable from both economic and environmental viewpoints. They can be formed by condensing orthodiamines with 1,2diketones. Facile synthesis of quinoxaline derivatives using o. The cdk15 inhibitor, also referenced under cas 40254908, controls the biological activity of cdk15. Tpzs are synthesized from glyoxal and 3,4diaminothiophene 1983bsf159. Currents activated by kainate or rsalphaamino3hydroxy5methyl4isoxazolepropionic acid ampa in xenopus oocytes were inhibited competitively by all the quinoxaline derivatives, with.
Quinoxaline derivatives are widely distributed in nature and many of them, such as the antibiotics, levomycin and actinomycin possess very useful biological activity. Galliumiii triflatecatalyzed synthesis of quinoxaline. A stability of 812 h is described for the quinoxaline derivatives in sample extracts. Therefore, the aim of this project was to synthesis some novel of 2,3substituted quinoxaline.
Molecules free fulltext new quinoxaline derivatives as. Quinoxalines and fused ring systems show diverse pharmacological activities. Tgase 2 also suppresses apoptosis via depletion of caspase 3 and cathepsin d. Quinoxaline 1,4dioxide compounds and desoxycarbadox quinoxaline 1,4dioxide compounds are antimicrobial agents that are used as animal growth promoters for livestock. Quinoxaline 1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine.
Synthesis and evaluation of new quinoxaline derivatives of. The reaction proceeds very cleanly at room temperature in a onepot procedure and free of side products. Chromophorelabeled quinoxaline derivatives as efficient. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. Microwaveassisted synthesis of quinoxaline derivatives using. Mar 21, 2016 with the wide use of qdnos, the toxicity and drug resistance gradually have become the disadvantages for further application of these promising compounds. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Food and drug administration fda since 1998 for the control of swine dysentery. The hydroxyl group was readily converted into a thiol function by treatment with phosphorus pentasulfide andor lawessons reagent in pyridine, and the subsequent. A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against m. 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. Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4.
Predicted data is generated using the us environmental protection agencys episuite. A catalyst free, greener and highly efficient method for the synthesis of a series of quinoxaline derivatives involving simple liquid assisted handgrinding in a mortar and pestle has been developed. Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. The molecular targets of quinoxaline derivatives, which is a step beyond simply looking at their activities, should be analyzed. A series of new quinoxaline derivatives of dehydroabietic acid daa were designed and synthesized as potential antitumor agents. Chromophores were embedded both at quinoxaline and triarylamine units, and their influence on photophysical and thermal properties was investigated. Quinoxaline derivatives doped by strong organic acid were effective as ph indicators for volatile amine detection, with lower detection limits than cinnamil.
Synthesis and antimicrobial activity of some new quinoxaline derivatives subba rami reddy sr, suryanarayana rao. A facile and simple catalyst free protocol has been developed for the condensation of 1,2diketones with aromatic 1,2diamines in polyethylene glycol peg, providing quinoxaline derivatives in. Further, the preparation of the quinoxaline derivative during extraction requires additional labor compared with the postcolumn derivatization. Synthesis and antimicrobial activity of some new quinoxaline. Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles. Pdf convenient methods for the synthesis of quinoxaline derivatives with the use of nucleophilic.
Interestingly, these methods for the preparation of the quinoxalines derivatives have none of the abovementioned drawbacks at all. Efficient synthesis of quinoxaline derivatives catalyzed by p. Derivatives catalyzed by ptoluenesulfonic acid under solventfree conditions. 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. 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. In this regard, a series of quinoxaline derivatives 117 was synthesized and biologically evaluated against cholinesterases ache and bche and as well as against. Bf3promoted electrochemical properties of quinoxaline in. The complexes of quinoxaline with several metal ions have been studied by various workers.
Due to a larger quinoidal character, the band gap of tpzcontaining polymers is smaller than that of the quinoxaline containing derivatives 2008mm6012. Electroluminescent materials comprising quinoxaline, triarylamine, and fluorophores such as carbazole, pyrene, and fluorene were prepared by using a key step involving a pdcatalyzed c. It is rare in natural state, but their synthesis is easy to perform. Thieno3,4bpyrazines tpzs, the thiophenecontaining analog of quinoxalines, are also popular acceptor units in polymer semiconductors. Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. Synthesis and antimicrobial activities of some novel. Pharmaceuticals free fulltext synthesis and antimicrobial. Therefore, inhibiting the activity of bche may be an effective way to control ad associated disorders. Theoretical investigation using dft of quinoxaline. Quinoxalines synthesis, reactions, mechanisms and structure.
An efficient protocol for the synthesis of quinoxaline. There are a wide range of quinoxaline derivatives with antimicrobial activity documented. A series of quinoxalinone derivatives were synthesized by the reaction of o. B3lyp6311g d,p methods are realized to obtain geometries and optimize the electronic properties, optical and photovoltaic parameters for some quinoxaline derivatives. 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. It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. Pdf new opportunities for the synthesis of quinoxaline derivatives.
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 novel quinoxaline carboxylic acid derivatives. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. 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. The 4acetoxybenzyl ester of pyrazinoic acid and 4acetoxybenzyl 2quinoxalinecarboxylate showed excellent activity against mtb mic ranges of less than 1. New quinoxaline derivatives were prepared by the reaction of 2hydroxyquinoxaline 1 and alkyl or alkylaminoalkyl halides in dimethylformamide using potassium carbonate as a base. Synthesis and antimicrobial activity of some new quinoxaline derivatives. Onepot and efficient protocol for synthesis of quinoxaline. We centred our discussion in the various drug patent applications of the quinoxaline and its derivatives. Design, synthesis, and characterization of quinoxaline derivatives. In this article we report the synthesis of quinoxaline derivatives in the presence of ibx. Accepted manuscript discovery of indeno1,2b quinoxaline derivatives as potential anticancer agents chihhua tseng, youren chen, cherngchyi tzeng, wangta liu, chonkit chou, chienchih chiu, yehlong chen pii.
Silicagelcatalyzed efficient synthesis of quinoxaline derivatives. The features introduced by this protocol, such as using a cheap and available organocatalyst, avoidance of. Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2dicarbonyl compounds in the presence of ibx in acetic acid. Solventfree quinoxaline synthesis catalyzed by ptoluene sulfonic acid. Quinoxaline derivative an overview sciencedirect topics. 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. Ecofriendly approach to access of quinoxaline derivatives.
The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the. Synthesis and neuropharmacological evaluation of some novel. Synthesis, reactions and biological activity of quinoxaline. Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible. Apr 21, 20 transglutaminase 2 tgase 2, a crosslinking enzyme, plays an important role in both prosurvival and antiapoptosis during oncogenesis. An efficient catalystfree protocol for the synthesis of quinoxaline. Accepted manuscript discovery of indeno1,2bquinoxaline derivatives as potential anticancer agents chihhua tseng, youren chen, cherngchyi tzeng, wangta.
Novel rearrangement of certain quinoxaline noxides to 6benzimidazolinones. Their structures were confirmed by using 1 h nmr, ir, and mass analysis. 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. Alzheimers disease ad is a progressive brain disorder which occurs due to lower levels of acetylcholine ach neurotransmitters, and results in a gradual decline in memory and other cognitive processes. However, cinnamil exhibited more diverse color profiles than the quinoxaline indicators when exposed to ammonia, trimethylamine, triethylamine, dimethylamine, piperidine and hydrazine. The applications are based firstly in the specific enzyme.
Results and discussion at first, ionic liquid 1,3disulfonic acid imidazolium chloride dsimcl was prepared by the reaction of. Synthesis of novel quinoxaline carboxylic acid derivatives for antimicrobial investigation m s a elgaby, m m f ismail b, y a ammarc. It is a colorless oil that melts just above room temperature. 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 are an important class of heterocyclic compounds, in which n. Synthesis and evaluation of quinoxaline derivatives as potential. Molecules 2019, 24, 1175 3 of 22 is a wellknown diarylurea multitargeted inhibitor of several kinases including raf, vegfr, ckit and pdgfr 17. Ganesh chandra nandi, subhasis samai, ram kumar, and. Design and synthesis of new quinoxaline derivatives as. Photovoltaic properties of solar cells based on fifteen organic dyes have been studied in this work. Lproline as an e cient organocatalyst for the synthesis of.
Synthesis of 2monosubstituted derivatives of quinoxalines in. This is a pdf file of an unedited manuscript that has been. A rapid, efficient, and reliable catalyst free procedure for the synthesis of quinoxaline derivatives in glycerol under focused microwave irradiation was developed. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. A library of quinoxaline derivatives were prepared to target. The stability of the quinoxaline derivatives, however, is also limited. Supplementary data are available free of charge at, as pdf file. Quinoxaline derivatives exhibit a broad spectrum of biological activity such as antibacterial24, antifungal5,6, antiviral 7, anticancer8, antitubercular9, antimalarial10 and antiinflammatory11.
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