Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines hct116 human colon carcinoma, hepg2. Quinoxaline is formed by the fusion of two aromatic. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinoxalines. Although quinoxaline itself is mainly of academic interest, quinoxaline. Synthesis of a quinoxalinecontaining benzoxazine from a. Gk showed a possibility that quinoxaline derivatives may be effective for anti cancer activity via tgase 2 inhibition. Synthesis, anticancer and cytostatic activity of some 6hindolo2,3bquinoxalines. Condensed quinoxalines were obtained by oxidative cyclisation of quinoxaline2carboxaldehyde hydrazone and phenylhydrazone using lead tetraacetate. Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived. Supplier of aroma chemicals, pharmaceutical and specialty chemical intermediates. Quinoxalines and fused ring systems show diverse pharmacological activities. These colorless antibiotics are derived from various species of streptomycetes and are highly active against grampositive bacteria.
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. Quinoxaline2carboxaldehyde was also used for the synthesis of a large number of new condensed quinoxalines and heteroaryl quinoxalines. The drug induced very low hemolysis, but its antiprotozoan activity was partially inhibited when mouse blood was added in the experiment against trypomastigotes, an effect that was specifically related to blood cells. Quinoxaline is a chemical compound that presents a structure that is similar to quinolone antibiotics. Since several years, our group developed quinoxalinic compounds. Among the synthesized compounds, in the imidazo1,2. Apr 21, 20 lc50 of gk showed greater efficacy as 4. Vl college of pharmacy 2, raichur, karnataka, india. Pdf anticancer effect of a quinoxaline derivative gk. Anticancer effect of a quinoxaline derivative gk as a transglutaminase 2 inhibitor. This chemicals molecular formula is c 14 h 14 clfn 8 and molecular weight is 251. Mar 12, 2012 before attempting detailed catalytic work, a noncatalytic reaction between ophenylenediamine 1 mmol, benzyl 1 mmol, and toluene 7 ml was examined and it was observed that, under the experimental conditions 25c, 2 h, no formation of quinoxaline was detected, indicating that from a practical point of view the reaction is not taking place in the absence of a catalyst table 2, entry 1. Antimicrobial activity of quinoxaline 1,4dioxide with 2 and. Predicted data is generated using the us environmental protection agencys episuite.
Although tumor hypoxia poses challenges against conventional cancer treatments, it provides a therapeutic target for hypoxiaactivated drugs. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. Quinoxaline 1,4dinoxide and the potential for treating. 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 quinoxaline dinoxide dcq blocks breast cancer metastasis in vitro. A quinoxaline derivative as a potent chemotherapeutic agent.
Quinoxaline2carboxylic acid an overview sciencedirect topics. We have synthesized a series of new compounds with a variety of modifications of lead. Quinoxaline is a nitrogen containing a heterocyclic compound formed by the fusion of two aromatic rings, benzene and pyrazine. The moiety is of substantial importance because of its wide array of pharmacological activities viz. Quinoxaline article about quinoxaline by the free dictionary. From anti inflammatory activity studies it was found that compounds showed significant activity.
Quinoxalines are considered as an important basis for anticancer drugs as they are proved to be selective adenosine triphosphate atp. Hypoxic cells which are found in solid tumors are resistant to anticancer drugs and radiation therapy. A simple and efficient protocol for the synthesis of. Cancers are among the leading causes of morbidity and mortality worldwide, responsible for 18. Cert if i ed that the thes is ent it led n synthesis and reactions of quinoxalines 11 submi t ted by shri keshav mohan is a bona fide work done by him under my guidance in the department of applied chemistry, cochin university of science and technology, and no part of this has. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. An efficient protocol for the synthesis of quinoxaline. Quinoxaline synonyms, quinoxaline pronunciation, quinoxaline translation, english dictionary definition of quinoxaline.
The present work reports the study of the antimicrobial activity of quinoxaline n,ndioxide and some derivatives against bacterial and yeast strains. Imamoto and coworkers have addressed this deficiency through the invention of quinoxp, which contains an electronwithdrawing quinoxaline architecture. Synthesis, reactions and biological activity of quinoxaline. Quinoxaline derivatives possess a broad spectrum of biological activities including anti bacterial, anti viral, anti inflammatory, anti cancer, and kinase inhibitors. The quinoxaline,6nitro2phenyl has the cas registry number 71896996.
Mesco college of pharmacy 1, karwan road, mustaidpura, hyderabad, andhra pradesh, india. Comperative study of isoflavone, quinoxaline and oxindole families of anti angiogenic agents. Different types of quinoxaline derivatives show antimicrobial activity. This highly reactive benzoxazine resin also exhibits low viscosity and good shelflife. Chemistry and pharmacological diversity of quinoxaline motifs as. Moreover, the use of quinoxaline based polymerssmall molecules in bulk heterojunction bhj devices led to power conversion efficiencies over 9%. Anti inflammatory activity of novel substituted quinoxaline heterocycles html full text. The structure of eapb0203 has been modulated and a new compound, eapb0503, exhibits an in vitro cytotoxic activity on melanoma cancer cell line 79 times higher than eapb0203. Quinoxaline derivatives exhibit a broad spectrum of biological activity such as antibacterial24, antifungal5,6, antiviral 7, anticancer8, anti tubercular9, antimalarial10 and anti inflammatory11. Chemistry and pharmacological diversity of quinoxaline motifs as anticancer agents. Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. Quinoxaline based materials are endowed with characteristics that are useful for large scale production in real world applications, such as easy synthetic procedures and excellent stability in air. Whats more, its systematic name is 6nitro2phenylquinoxaline.
Heterocyclic compounds are a class of substances, which play a critical role in modern drug discovery being incorporated in the structure of a large variety. Quinoxaline structure acts as a precursor to assembly a large number of new compounds for diverse applications. The synthesis of quinoxalines has been intensively studied in the past. Anticancer effect of a quinoxaline derivative gk as a.
The nci dictionary of cancer terms features 8,545 terms related to cancer and medicine we offer a widget that you can add to your website to let users look up cancerrelated terms. Cancer, drug discovery, synthesis, quinoxaline, heterocyclic compounds, biological activity. In this study, we investigated the roles of tk1 and tymp on a thymidine quinoxaline. Various 6aralkyl9substituted6hindolo2,3bquinoxalines were.
Action of quinoxaline 1, 4dinoxides against clostridium perfringens and. The cytotoxicity against llcmk 2 cells provided selective indices above one for all of the parasite forms. Quinoxalinebisarylurea 2 figure1 has been reported by goring et al. Synthesis and reactions of quinoxalines dyuthi cusat. For example, they can be used against bacteria, fungi, virus, leishmania, tuberculosis, malaria, cancer, depression, and neurological activities, among others. Onepot and efficient protocol for synthesis of quinoxaline. Jan 24, 2014 although tumor hypoxia poses challenges against conventional cancer treatments, it provides a therapeutic target for hypoxiaactivated drugs.
It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. 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. High levels of thymidine kinase 1 tk1 and thymidine phosphorylase tymp are key molecular targets by thymidine therapeutics in cancer treatment. These chapters give comprehensive coverage of all the methods of the synthesis of quinoxalines and the important quinoxalinecontaining ring systems such as thiazolo3,4a, pyrrolo1,2a, and imidazo1,5aquinoxalines. A wealth of experience, expertise and knowledge has allowed augustus to bridge the gulf in expectation and trust between growers and users of natural ingredients. Several quinoxaline derivatives were reported to be potent and.
Anticancer activity of a thymidine quinoxaline conjugate is. A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employing lproline as a catalyst in water. Delong chemicals america, llc is an extension of shijiazhuang lida chemical co, ltd to north america, a leading supplier and manufacturer of aroma chemicals, serving the industries of food, tobacco and perfume, while also providing intermediates, custom synthesis and custom manufacturing for. Perhaps the presence of och 3 on phenyl nucleus attached to second position of the quinoxaline nucleus may be responsible for marked anti inflammatory activity from anti inflammatory activity evaluation, it. The human breast cancer cell lines mcf7 p53 wildtype and mdamb231. Augustus oils ltd, in harmony with nature to present it at its best. Additionally, quinoxalines were found to induce apoptosis as a mechanism for their anticancer activity 11,12. Echinomycin 1 has been shown to be an antitumor agent and to have antiviral. In this study, we investigated the roles of tk1 and tymp on a thymidine quinoxaline conjugate to. The in vitro cytotoxic activities of 7 dialkylaminomethyl benzog quinoxaline 5, 10 dione derivatives 291ae was evaluated against panel of human cancer cell lines. The quinoxaline structural nucleus renders all these activities possible. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. In order to improve the drug armamentarium against chagas disease, in the present study we describe the synthesis of the compound 3chloro7methoxy2methylsulfonyl quinoxaline quinoxaline 4 and its activity, alone or in combination with benznidazole, against trypanosoma cruzi in vitro. Food and drug administration fda since 1998 for the control of swine dysentery.
A quinoxaline derivative as a potent chemotherapeutic. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. Chapter five describes many new methods for the construction of quinoxaline macrocycles, which are important in. Recent development of quinoxaline based polymerssmall. Synthesis, anticancer and cytostatic activity of some 6hindolo2,3b. Any one of a series of complex nitrogenous bases obtained by the union of certain aniline derivatives with glyoxal or with certain ketones. Quinoxalines synthesis, reactions, mechanisms and structure.
Synthesis and properties of quinoxalinecontaining benzoxazines. This can be relieved in most cases through medicines and other treatments. Pelagia research library known to inhibit the growth of grampositive bacteria and are also active against various transplantable tumors. Quinoxaline 1,4dioxides as anticancer and hypoxiaselective drugs. The objective of chemotherapy in cancer is the selection of drugs and dose levels, which will eradicate disseminated cancer cells, without causing severe host toxicity. Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles. The dual roles of tymp as a tumor growth factor and a key activation enzyme of anticancer metabolites resulted in a mixed outcome in cancer patients. The human breast cancer cell lines mcf7 p53 wildtype and mdamb231 p53 mutant were. Quinoxaline1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine.
Design and synthesis of new quinoxaline derivatives as. Anticancer activity of a thymidine quinoxaline conjugate. Pharmacology of eapb0203, a novel imidazo 1,2a quinoxaline derivative with anti tumoral activity on melanoma. 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 an important heterocyclic nucleus with a wide spectrum of biological activities, and recently much attention has been found on anticancer drug discovery based on this class. Delong chemicals america, llc is an extension of shijiazhuang lida chemical co, ltd to north america, a leading supplier and manufacturer of aroma chemicals, serving the industries of food, tobacco and perfume, while also providing intermediates, custom synthesis and custom. Antimicrobial activity of quinoxaline 1,4dioxide with 2.
Some substituted quinoxaline 1, 4dinoxides 289 and tested for tumour inhibiting activity and highly active as a cytotoxic agent with highest hypoxic cytotoxicity 26, 64, 65 and pyridine2carboxylic acid n7fluoropyrrolo1,2a quinoxalin4yl hydrazide 290b derivatives 290a, in panel of cancer cell lines, a breast cancer cell. Heterocyclic compounds are a class of substances, which play a critical role in modern drug discovery being incorporated in the structure of a large variety of drugs used in many different types of diseases. Quinoxaline 1,4dioxide compounds and desoxycarbadox quinoxaline 1,4dioxide compounds are antimicrobial agents that are used as animal growth promoters for livestock. It is a colorless oil that melts just above room temperature. Here, we studied the effect of the hypoxiaactivated synthetic quinoxaline dinoxide dcq against breast cancer metastasis and identified the underlying mechanisms. Quinoxaline1,4dioxide compounds and desoxycarbadox quinoxaline1,4dioxide compounds are antimicrobial agents that are used as animal growth promoters for livestock. Quinoxaline 4 was found to be strongly active against trypanosoma cruzi y strain and more effective against the proliferative forms. It is rare in natural state, but their synthesis is easy to perform. Quinoxaline2carboxamide c9h7n3o cid 78857 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Its molecular formula is c 8h 6n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. International journal of pharmtech research coden usa. Quinoxaline 1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. These novel derivatives of indolo2,3b quinoxalines also posses structural similarities with antipsychotic drug aripiperazole.
Thus, for effective anticancer chemotherapy, it is important to. In addition, a novel 8chloro44chlorophenylpyrrolo1,2aquinoxaline has been reported to induce selective antiproliferative activity in breast cancer cell lines. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Quinoxaline 2carboxamide c9h7n3o cid 78857 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Pain is experienced by 55% of patients undergoing anticancer treatment and by 66% of patients who have advanced, metastatic, or terminal disease. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. Use this link for bookmarking this species for future reference. Quinoxaline is a white crystalline powder, with a melting point 2930 c and a molecular formula c 8 h 6 n 2.
Synthesis and reactions of some novel quinoxalines for anticancer. Moreover, the national cancer institute nci selected 20 compounds that were submitted for anticancer screening against 60 types of cancer cell. It is a light yellow crystalline solid that is soluble in water. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals, and antibiotics such as olaquindox, carbadox. Quinoxaline, a fused heterocycle of benzene and pyrazine rings has gained considerable attention in the field of contemporary medicinal chemistry. Mar 21, 2015 high levels of thymidine kinase 1 tk1 and thymidine phosphorylase tymp are key molecular targets by thymidine therapeutics in cancer treatment.
Inhibition of angiogenesis and inflammation by an extract of red clover trifolium pratense l. 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. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Design and synthesis of new quinoxaline derivatives as anticancer. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on condensed pyrazines by cheeseman. Synthesis, in vitro anticancer screening and radiosensitizing. Food and drug administration fda since 1998 for the control of. Exploration of quinoxaline derivatives as antimicrobial and. 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. Quinoxaline definition of quinoxaline by the free dictionary. Quinoxaline structure acts as a precursor to assembly a large number of new compounds for diverse applications 1. Quinoxaline medical definition merriamwebster medical.
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