Chemistry and pharmacological diversity of quinoxaline motifs as anticancer agents. Condensed quinoxalines were obtained by oxidative cyclisation of quinoxaline2carboxaldehyde hydrazone and phenylhydrazone using lead tetraacetate. The in vitro cytotoxic activities of 7 dialkylaminomethyl benzog quinoxaline 5, 10 dione derivatives 291ae was evaluated against panel of human cancer cell lines. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. It is a light yellow crystalline solid that is soluble in water. Quinoxaline is formed by the fusion of two aromatic. Moreover, the use of quinoxaline based polymerssmall molecules in bulk heterojunction bhj devices led to power conversion efficiencies over 9%. Synthesis and properties of quinoxalinecontaining benzoxazines. 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. Here, we studied the effect of the hypoxiaactivated synthetic quinoxaline dinoxide dcq against breast cancer metastasis and identified the underlying mechanisms. Exploration of quinoxaline derivatives as antimicrobial and. A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employing lproline as a catalyst in water. Synthesis, anticancer and cytostatic activity of some 6hindolo2,3b. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented.
Anticancer effect of a quinoxaline derivative gk as a transglutaminase 2 inhibitor. Vl college of pharmacy 2, raichur, karnataka, india. Anticancer activity of a thymidine quinoxaline conjugate. Quinoxaline 2carboxamide c9h7n3o cid 78857 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. 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. Quinoxaline2carboxaldehyde was also used for the synthesis of a large number of new condensed quinoxalines and heteroaryl quinoxalines. It is a heterocyclic compound containing a ring complex made up of benzene ring and a pyrazine ring. Food and drug administration fda since 1998 for the control of. It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. Pain is experienced by 55% of patients undergoing anticancer treatment and by 66% of patients who have advanced, metastatic, or terminal disease. Pdf anticancer effect of a quinoxaline derivative gk. Quinoxaline derivatives possess a broad spectrum of biological activities including anti bacterial, anti viral, anti inflammatory, anti cancer, and kinase inhibitors. 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. Quinoxalines synthesis, reactions, mechanisms and structure.
Supplier of aroma chemicals, pharmaceutical and specialty chemical intermediates. Moreover, the national cancer institute nci selected 20 compounds that were submitted for anticancer screening against 60 types of cancer cell. Quinoxaline1,4dioxide compounds and desoxycarbadox quinoxaline1,4dioxide compounds are antimicrobial agents that are used as animal growth promoters for livestock. 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. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Synthesis, reactions and biological activity of quinoxaline. From anti inflammatory activity studies it was found that compounds showed significant activity. Design and synthesis of new quinoxaline derivatives as. Action of quinoxaline 1, 4dinoxides against clostridium perfringens and. Anticancer drugs particularly affect cells in active division and, in general, normal and neoplastic cells cannot be differentiated. Quinoxaline2carboxamide c9h7n3o cid 78857 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Cancers are among the leading causes of morbidity and mortality worldwide, responsible for 18. 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. It is a colorless oil that melts just above room temperature.
Anticancer activity of a thymidine quinoxaline conjugate is. Quinoxaline, a fused heterocycle of benzene and pyrazine rings has gained considerable attention in the field of contemporary medicinal chemistry. Synthesis and reactions of some novel quinoxalines for anticancer. Design and synthesis of new quinoxaline derivatives as anticancer. Quinoxaline medical definition merriamwebster medical.
The present work reports the study of the antimicrobial activity of quinoxaline n,ndioxide and some derivatives against bacterial and yeast strains. Quinoxaline 1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. For example, they can be used against bacteria, fungi, virus, leishmania, tuberculosis, malaria, cancer, depression, and neurological activities, among others. Quinoxaline structure acts as a precursor to assembly a large number of new compounds for diverse applications 1. Quinoxaline is a nitrogen containing a heterocyclic compound formed by the fusion of two aromatic rings, benzene and pyrazine. Gk showed a possibility that quinoxaline derivatives may be effective for anti cancer activity via tgase 2 inhibition. Mar 21, 2015 high levels of thymidine kinase 1 tk1 and thymidine phosphorylase tymp are key molecular targets by thymidine therapeutics in cancer treatment. Additionally, quinoxalines were found to induce apoptosis as a mechanism for their anticancer activity 11,12. These colorless antibiotics are derived from various species of streptomycetes and are highly active against grampositive bacteria. Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived. Its molecular formula is c 8h 6n 2, formed by the fusion of two aromatic rings, benzene and pyrazine.
Quinoxaline2carboxylic acid an overview sciencedirect topics. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines hct116 human colon carcinoma, hepg2. 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. 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. A simple and efficient protocol for the synthesis of. Among the synthesized compounds, in the imidazo1,2. A quinoxaline derivative as a potent chemotherapeutic. 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. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on condensed pyrazines by cheeseman. Echinomycin 1 has been shown to be an antitumor agent and to have antiviral. 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. Synthesis and reactions of quinoxalines dyuthi cusat. 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.
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. These novel derivatives of indolo2,3b quinoxalines also posses structural similarities with antipsychotic drug aripiperazole. Chapter five describes many new methods for the construction of quinoxaline macrocycles, which are important in. 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.
Quinoxaline structure acts as a precursor to assembly a large number of new compounds for diverse applications. Quinoxaline and its derivatives are very important class of nitrogen containing heterocycles. 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. 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. Different types of quinoxaline derivatives show antimicrobial activity. Jan 24, 2014 although tumor hypoxia poses challenges against conventional cancer treatments, it provides a therapeutic target for hypoxiaactivated drugs. Any one of a series of complex nitrogenous bases obtained by the union of certain aniline derivatives with glyoxal or with certain ketones. Thus, for effective anticancer chemotherapy, it is important to. Inhibition of angiogenesis and inflammation by an extract of red clover trifolium pratense l. This can be relieved in most cases through medicines and other treatments. The quinoxaline structural nucleus renders all these activities possible. Various 6aralkyl9substituted6hindolo2,3bquinoxalines were. Synthesis, anticancer and cytostatic activity of some 6hindolo2,3bquinoxalines.
Although quinoxaline itself is mainly of academic interest, quinoxaline. Use this link for bookmarking this species for future reference. 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. Apr 21, 20 lc50 of gk showed greater efficacy as 4. Quinoxalinebisarylurea 2 figure1 has been reported by goring et al. Quinoxaline 1,4dinoxide and the potential for treating. 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. Antimicrobial activity of quinoxaline 1,4dioxide with 2 and.
Quinoxaline is a chemical compound that presents a structure that is similar to quinolone antibiotics. It is rare in natural state, but their synthesis is easy to perform. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Although tumor hypoxia poses challenges against conventional cancer treatments, it provides a therapeutic target for hypoxiaactivated drugs. Imamoto and coworkers have addressed this deficiency through the invention of quinoxp, which contains an electronwithdrawing quinoxaline architecture. The synthesis of quinoxalines has been intensively studied in the past. Quinoxalines and fused ring systems show diverse pharmacological activities. Whats more, its systematic name is 6nitro2phenylquinoxaline. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. Quinoxaline is a white crystalline powder, with a melting point 2930 c and a molecular formula c 8 h 6 n 2. Quinoxaline is well known for its broad coverage in the field of medicine as well as for its application in the pharmaceuticals. Augustus oils ltd, in harmony with nature to present it at its best. Anticancer effect of a quinoxaline derivative gk as a.
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. Several quinoxaline derivatives were reported to be potent and. 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. Quinoxaline1 2 also called 1,4benzodiazine, benzoparadiazine, phenpiazine and benzopyrazine. We have synthesized a series of new compounds with a variety of modifications of lead. 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. Anti inflammatory activity of novel substituted quinoxaline heterocycles html full text. Quinoxaline 4 was found to be strongly active against trypanosoma cruzi y strain and more effective against the proliferative forms. 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. Quinoxaline synonyms, quinoxaline pronunciation, quinoxaline translation, english dictionary definition of quinoxaline. This chemicals molecular formula is c 14 h 14 clfn 8 and molecular weight is 251. 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. This highly reactive benzoxazine resin also exhibits low viscosity and good shelflife.
Cancer, drug discovery, synthesis, quinoxaline, heterocyclic compounds, biological activity. Antimicrobial activity of quinoxaline 1,4dioxide with 2. Synthesis, in vitro anticancer screening and radiosensitizing. Pelagia research library known to inhibit the growth of grampositive bacteria and are also active against various transplantable tumors. In this study, we investigated the roles of tk1 and tymp on a thymidine quinoxaline. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinoxalines. Mesco college of pharmacy 1, karwan road, mustaidpura, hyderabad, andhra pradesh, india. Recent development of quinoxaline based polymerssmall. A quinoxaline derivative as a potent chemotherapeutic agent. 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. Onepot and efficient protocol for synthesis of quinoxaline. Quinoxaline 1,4dioxides as anticancer and hypoxiaselective drugs. Quinoxaline definition of quinoxaline by the free dictionary. In this study, we investigated the roles of tk1 and tymp on a thymidine quinoxaline conjugate to.
Comperative study of isoflavone, quinoxaline and oxindole families of anti angiogenic agents. The human breast cancer cell lines mcf7 p53 wildtype and mdamb231. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals, and antibiotics such as olaquindox, carbadox. In addition, a novel 8chloro44chlorophenylpyrrolo1,2aquinoxaline has been reported to induce selective antiproliferative activity in breast cancer cell lines. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. Food and drug administration fda since 1998 for the control of swine dysentery. An efficient protocol for the synthesis of quinoxaline. The quinoxaline,6nitro2phenyl has the cas registry number 71896996. The human breast cancer cell lines mcf7 p53 wildtype and mdamb231 p53 mutant were. Quinoxaline 1,4dioxide compounds and desoxycarbadox quinoxaline 1,4dioxide compounds are antimicrobial agents that are used as animal growth promoters for livestock.
The moiety is of substantial importance because of its wide array of pharmacological activities viz. Chemistry and pharmacological diversity of quinoxaline motifs as. 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. International journal of pharmtech research coden usa. High levels of thymidine kinase 1 tk1 and thymidine phosphorylase tymp are key molecular targets by thymidine therapeutics in cancer treatment. Predicted data is generated using the us environmental protection agencys episuite. Quinoxaline article about quinoxaline by the free dictionary. Synthesis of a quinoxalinecontaining benzoxazine from a.
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. Since several years, our group developed quinoxalinic compounds. Pharmacology of eapb0203, a novel imidazo 1,2a quinoxaline derivative with anti tumoral activity on melanoma. 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. The cytotoxicity against llcmk 2 cells provided selective indices above one for all of the parasite forms.