The reaction could be carried out with a substratetocatalyst molar ratio as high as in undegassed. Pdf different heterocyclic analogues were evaluated for their. Synthesis and biological activity investigation of some. Here we describe the synthesis and antiviral activity evaluation of two compounds based on the quinoline scaffold, which has shown potential for the development of molecules with various. There are multiple ways to synthesize quinoline, one of which is the combes quinoline synthesis. The present study investigated the antioxidant effect of a new class of quinoline derivatives ad on assays in vitro.
R 5 is selected from the methyl, ethyl, npropyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, npropylthio, methylsulphinyl, ethylsulphinyl, fluoro, chloro, bromo, trifluoromethyl, and och x f y. The parent compound 18 and new quinoline derivatives 1926 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using edcmediated peptide. A novel and efficient method for the generation of alkyl radicals and the alkylation of quinoline and pyridine derivatives under mild conditions has been developed. Isoquinoline is a heterocyclic aromatic organic compound. Transitionmetal free quinoline synthesis from acetophenones and anthranils via sequential onecarbon homologationconjugate additionannulation cascade. Many alkaloids, such as quinine and fagarine, and drugs, such as atophan cinchophen, enteroseptol iodochlorhydroxyquin, chloroquine, and primaquine, are derivatives of quinoline, as are several cyanine dyes and. Structural modifications of quinolinebased antimalarial. Synthesis, anticonvulsant and antihypertensive activities of 8. Quinoline derivatives, 6hydroxyquinoline, 6methoxyquinoline, 6bromoquinoline, 5nitroquinoline, 6nitroquinoline, 8aminoquinoline, mumbai, indi created date 8312010 10. Quinoline derivatives quinoline derivatives derivative. Biological activities of quinoline derivatives bentham science. Microwave enhanced solvent free synthesis of a library of quinoline derivatives. Quinoline derivatives are prevalent in a variety of pharmacologically active synthetic and natural compounds.
It is a colorless hygroscopic liquid with a strong odor. Biological activities of quinoline derivatives bentham. Aminoquinolines are derivatives of quinoline, most notable for their roles as antimalarial drugs. The significance of quinoline heterocyclic nucleus in the field of medicinal chemistry research is worth mentioning. Quinoline article about quinoline by the free dictionary. The recent increase in development of chloroquineresistant strains of plasmodium falciparum and failure of vaccination program against malaria have fuelled the drug discovery program against this old and widespread disease. Duringthepasttenyearsmanyderivatives ofquinoline4carboxylicacidhavebeenprepared,particularly ofthe2phenylquinoline4carboxylicacid. Quinoline definition of quinoline by the free dictionary.
Quinoline derivatives have been known to possess a variety of biological activities such as antitumor 4, antimalarial 5, antiplatelet 6, antidepressant 7, antiulcer 8 and cardiac stimulant 9. So far, there are no effective antivirals licensed to treat this virus. Pdf an efficient synthesis of isoindolo2,1aquinoline. Quinoline and its fused heterocyclic derivatives tested with diverse pharmacological activity constitute an important class of compounds for new drug development. Prion diseases are invariably fatal neurodegenerative diseases, in which the infectious agent consists of prpsc, a pathogenic misfolded isoform of the normal cellular prion protein prpc. Quinoline derivatives constitute an important class of compounds for new drug development. Synthesis of benzo f quinoline and its derivatives.
Quinoline derivatives, which widely occur in nature, especially alkaloids, have become an important skeleton in synthetic chemistry due to their variety of applications in medicinal, bioorganic, and industrial chemistry. The wide range of its application has drawn an immense attention to the researchers to generate various quinoline derivatives, which may possess novel therapeutic efficacy. The synthesis of quinoline derivatives has been prevalent in biomedical studies due to the efficiency of the synthetic methods as well as the relative lowcost production of these compounds, which can also be produced in large scales. Potential exposure to quinoline may occur from the inhalation of cigarette smoke. Download fulltext pdf download fulltext pdf quinoline. An environmentally friendly and highly efficient procedure gives 2,4disubstituted quinoline derivatives by a simple alkynylationcyclization reaction of 2aminoaryl ketones with phenylacetylenes in the presence of indiumiii trifluoromethanesulfonate inotf 3 under microwave irradiation and solvent free conditions. Quinoline appears as a colorless liquid with a peculiar odor. The quinoline 5,8diones are an important class of compounds with a wide spectrum of biological activites such as antibacterial, antiasthmatic, antifungal, antitumour and antiparasitic agents. Indispensability of quinoline moiety in the field of. Itis a colorless hygroscopic liquid with a strong odor. Quinoline and quinolinone ring systems are present in a diverse array of natural products such as tecleabine, tecleoxime, pancratistatin, plakinidine and. Quinoline is the simplest member of the quinoline class of compounds, comprising a benzene ring ortho fused to c2 and c3 of a pyridine ring. Acute shortterm inhalation exposure to quinoline vapors irritates the eyes, nose.
Recent studies of antioxidant quinoline derivatives. Depending upon the location of the amino group, they can be divided into. The screening of antimicrobial activity of these synthesized compounds was done in vitro against some gram positive and gram negative strains of bacteria as well as fungal strains in n, ndimethyl formamide. Quinoline derivatives are probably best known for their diverse pharmacological properties marella et al. Quinoline is used as a solvent for sulfur and phosphorus and in the decarboxylation of aromatic acids and other reactions. Us6875869b2 process for the manufacture of quinoline.
Aged samples, if exposed to light,become yellow and later brown. Interestingly, more than twenty five alkaloids have been isolated and characterized either from the yellow cinchona i. As a large number of experimental and theoretical studies have shown that the quinoline ring system is an. The reaction was carried out in solvent free conditions under microwave. A process for the preparation of the compounds of general formula i wherein r is selected from methyl, ethyl, npropyl, isopropyl, nbutyl, isobutyl, sec. Antiviral activity of novel quinoline derivatives against. Here we describe the screening of a series of polyquinolines and quinolines linked to a large variety of terminal groups for their. Applications of quinoline derivatives are fast spreading from anticancer drugs to almost every branch of medicinal chemistry. Apr 15, 2020 quinoline, any of a class of organic compounds of the aromatic heterocyclic series characterized by a doublering structure composed of a benzene and a pyridine ring fused at two adjacent carbon atoms.
Background quinoline and its derivatives have received considerable attention because of their potential activities such as anticancer 19, antiinflammatory 1012, antioxidant, and other biological activities 17. Over 200 biologically active quinoline and quinazoline alkaloids are identified. A prominent example is quinine, an alkaloid found in plants. The present invention relates to a pharmaceutical composition comprising novel quinoline derivatives, their preparation, and people.
New quinoline 2one derivatives were synthesized by reaction of 4,7dimethyl coumarin i with nitric acid in the presence of concentrated sulfuric acid to afford 4,7dimethyl6nitrocoumarin ii and 4,7dimethyl8nitrocoumarin iii. In contextorganic compoundlangen terms the difference between quinoline and quinolone is that quinoline is organic compound any of a class of aromatic heterocyclic compounds containing a benzene ring fused with a pyridine ring. Quinoline derivatives represent a large number of antiproliferative agents exhibiting cytotoxicity through dna intercalation, causing interference in the replication process ryckebusch et al. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. Cyclization of 2 in refluxing diphenylether afforded oxoquinoline 3. Antimalarial agents generally belong to the class of quinoline which acts by interfering with heme metabolism. The straightforward synthesis of new isoindolo2,1a quinoline derivatives from 2,4disubstituted 1,2,3,4tetrahydroquinolines bearing a furan fragment via the intramolecular diels alder reaction is reported. Introduction alaria, one of the most infectious diseases of mankind in the world, is wide spread in more than 90 countries and affecting around 40% of the worlds population. On the basis of the original lead neocryptolepine or 5methyl5hindolo2,3b quinoline, an alkaloid from cryptolepis sanguinolenta, derivatives were prepared using a biradical cyclization methodology and screened for their antimalarial activity and cytotoxicity on human mrc5 cells. Quinoline derivatives as possible lead compounds for anti.
A series of quinoline 4methyl ester derivatives was synthesized by wu et al58 and evaluated their activity as human nonpancreatic secretory phospholipase a2 inhibitors. Synthesis of derivatives of 2 phenyl quinoline 4 carboxylic acid. Quinoline and quinolinone ring systems are present in a diverse array of natural products such as tecleabine, tecleoxime, pancratistatin, plakinidine and quinine. Nov 09, 2012 quinoline is a heterocyclic aromatic organic compound with the chemical formula c9h7n. The compound ii was treated with hydrazine hydrate 80% in pyridine to give n amino4,7dimethy 6nitroquinoline2one iv. Several quinoline derivatives isolated from natural resources or prepared synthetically are significant with respect to medicinal chemistry and biomedical use. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities.
General description quinoline is a heterocyclic aromatic organic compound with the chemical formula c 9 h 7 n. Over the past three decades many variously substituted derivatives of quinoline. A few quinoline derivatives 42 developed by manera et al. Friedlander prepared quinoline in 1882 by the condensation of o aminobenzaldehyde with acetaldehyde in the presence of sodium hydroxide. Antioxidant effect of quinoline derivatives containing or. All synthesized quinoline derivatives were screened for anti bacterial activity using dmf. An aromatic organic base, c9h7n, having a pungent tarlike odor, synthesized or obtained from coal tar, and used as a food preservative and in making antiseptics, drugs, and dyes. Several alkaloid quinoline compounds found in plants are important medicines. A mild, efficient, and general method for the synthesis of benzof quinoline and benzoaphenanthridine derivatives by a three.
Lipid peroxidation, thiol peroxidaselike and free radical scavenging activities were determined to evaluate antioxidant activity of compounds. Design, synthesis and potential antiproliferative activity of some. Quinoline derivatives, 6hydroxyquinoline, 6methoxyquinoline. External oxidantfree alkylation of quinoline and pyridine. Quinoline reagent grade, 98% 2,3benzopyridine sigma. Pdf microwave enhanced solventfree synthesis of a library. The free legands and its metal complexes have been tested in. The decomposition of quinoline and its derivatives have been enhanced by using either the free or immobilized cells of degrading microorganisms such as burkholderia pickettii wang et al. In our previous research on the positive inotropic activity of quinolines 10, 3,4dihydro2 1h quinoline compound i showed a slight. Quinolines have antiseptic, antipyretic, and antiperiodic properties and are used as antimalarials and for preparing other antimalarial drugs. This strategy allows the direct alkylation of heteroaromatics in the absence of an external oxidant. The reaction could be carried out with a substratetocatalyst molar ratio as high as in undegassed methanol.
Quinoline is only slightly soluble in cold water but dissolvesreadily in hot water and most organic solvents. A versatile heterocyclic article pdf available in saudi pharmaceutical journal 211. Airstable and phosphinefree iridium catalysts for highly. A series of quinoline derivative 50 was synthesized in.
The quinoline derivatives 7af were synthesized from commercially available 4amino3bromobenzonitrile 1, which was condensed with ethoxymethylenemalonate by refluxing in toluene to yield cluster 2 scheme 1. A possible reaction mechanism for the formation of the product is proposed based on further experimental results. This sequential transformation was efficient, conducted under metal free and mild reaction conditions, and yielded corresponding benzofuro3,2cquinolines in high yields. Quinoline derivatives, 6hydroxyquinoline, 6methoxyquinoline, 6bromoquinoline, 5nitroquinoline, 6nitroquinoline, 8aminoquinoline, mumbai, india. Feb 09, 2018 the oxy derivatives of the quinoline homologies are best obtained from the aniline derivatives of. Dengue virus causes dengue fever, a debilitating disease with an increasing incidence in many tropical and subtropical territories. A variety of conditions were employed in the synthesis.
Pdf recent studies of antioxidant quinoline derivatives. Quinoline breaks down quickly in the atmosphere and water. In our previous research on the positive inotropic activity of quinolines 10, 3,4dihydro2 1h quinoline. A variety of research have demonstrated that quinoline and its derivatives have shown cytotoxic activity by inhibiting pi3kpkb, epidermal growth factor receptor, mitogen. Antioxidant effect of quinoline derivatives containing or not. The chloroquine 2 10 is the most famous drug containing this active ingredient resulted in control and treatment of malaria for decades 7. Aged samples, especially if exposed to light, become yellow and later brown. R 4 means hydrogen atom and pharmaceutically acceptable inorganic or organic anions. R 5 means methyl, ethyl, npropyl, isopropyl, methoxygroup, ethoxygroup, chlorine, bromine atom, cf 3 and.
Quinoline is a heterocyclic aromatic organic compound with the chemical formula c 9 h 7 n. Quinoline 91225 hazard summary quinoline is used mainly as an intermediate in the manufacture of other products. The chlorination of 3 with pocl3 provided 4chloroquinoline 4 in good yield. An efficient method for the synthesis of benzofquinoline. It is a mancude organic heterobicyclic parent, a member of quinolines, an azaarene and an orthofused heteroarene. In vitro biological evaluation indicated that such type of compounds showed excellent antileukemia activity and selectivity, and therefore may offer a promising hit compound. As a large number of experimental and theoretical studies have shown that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with exciting biological activities. Quinoline itself has few applications, but many of its. Nandha department of chemistry, physical chemistry laboratory, saurashtra university, rajkot360005, india author for correspondence abstract some novel derivatives of quinoline have been synthesized and their structures were confirmed by ir 1h. Pdf biological activities of quinoline derivatives. Discovery of a potent and selective phosphodiesterase 5 inhibitor for the treatment of alzheimers disease jole fiorito, a faisal saeed, a hong zhang, a agnieszka staniszewski, a yan feng, a yitshak i.
A brief history of quinoline as antimalarial agents. Synthesis and biological evaluation of quinoline derivatives. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. Shortly after the isolation of quinoline from coal. Until now, no pharmacological options exist for these novel pathogens. Among other reasons, quinoline derivatives owe their popularity.
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