Nov 19, 2018 the development of different classes of porous polymers by linking organic molecules using new chemistries still remains a great challenge. Design, synthesis and anticancer evaluation of novel. Synthesis, characterization and apoptotic activity of. By combining the structural features of quinazoline and sulfonamides, novel hybrid compounds 221 were synthesized using a simple and convenient method. A cellpermeable quinazoline compound that augments the cytostatic effects of rapamycin and acts as an autophagy stimulator both in mammalian cultures in vitro and in a drosophila melanogaster hd model in vivo. Based on linagliptin, this study discusses the design, synthesis and biological evaluation of spiro cyclohexane1,2 quinazoline scaffold hybridized with various heterocyclic ring systems through different atomic spacers as a highly potent dpp4 inhibitors. The synthesis of a range of 1hquinazoline4ones is shown in scheme 1.
Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives. We quickly realized that the cyclizations were snar reactions and not srn1 substitutions. Synthesis of some quinazoline derivatives was carried out with their plant protection capabilities in mind. Synthesis and evaluation of some new 4, 6 disubstituted quinazoline derivatives for antimicrobial and antifungal activities chavan b. Synthesis and biological evaluation of quinazoline4thiones. The development of different classes of porous polymers by linking organic molecules using new chemistries still remains a great challenge. Synthesis of quinazoline2,41 h,3 hdiones from carbon dioxide and 2aminobenzonitriles using bmimoh as a homogeneous recyclable catalyst. Synthesis of porous covalent quinazoline networks cqns. Synthesis and evaluation of some new 4, 6 disubstituted.
Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolinones. Jan 01, 2012 2 ethoxy 43h quinazolinone 1 was synthesized and allowed to react with various halides, namely. Reduction of this with zinc and dilute acetic acid gave quinozoline in. Synthesis, characterization and apoptotic activity of quinazolinone schiff base derivatives toward. A new and facile preparation of quinazoline2,41h,3hdiones was first reported which was the condensation of aromatic oaminonitriles with dmf or n,ndiethylformamide in the presence of zncl2 0. Design and synthesis of sulphonyl acetamide analogues of. Synthesis of quinazoline 2,41 h,3 hdiones from carbon dioxide and 2aminobenzonitriles using bmimoh as a homogeneous recyclable catalyst. The syntheses of 17 substances from this group among them 6 new ones have been complete. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline.
Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Quinazoline is a mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms. A simple and efficient coppercatalyzed approach to quinazoline derivatives has been developed, and the protocol uses readily available substituted 2bromophenylmethylamines and amides as the starting materials, and the cascade reactions were performed under air via sequential ullmanntype coupling and aerobic oxidation without addition of any ligand or additive. Hydrogenation of the obtained quinazoline afforded 6chloro4,5dihydrotetrazolo1,5a quinazoline. An acetylhydrazide derivative containing a quinazoline nucleus has been utilized to design and synthesize a series of 2,4disubstituted quinazolines via reaction with several carbon electrophiles including 4methoxybenzaldehyde and carbon disulfide. The research on biological activity of quinazoline compounds started when the compound 2methyl1,3aryl4quinazoline derivative was synthesized. Unfortunately, classic chemical synthesis does not provide an opportunity for the formation of n. A series of sulphonyl acetamide analogues were generated on the quinazoline ring through a multistep reaction starting from 2mercapto3hquinazolin4one. Synthesis and antimicrobial activity of some new quinazoline. Srn1 substitutions issn 15517012 page 434 arkat usa, inc. May 19, 2017 reaction of 5aminotetrazole triethylammonium salt and 2fluoro6chlorobenzaldehyde resulted in the formation of 6chlorotetrazolo1,5a quinazoline instead of the expected azomethine. Synthesis and biological evaluation of quinazoline4thiones lenka kubicov.
In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. A brief survey about biological importance of quinazoline and thier derivatives revealed that a large number of publications began to appear after 1960s. Synthesis, characterization and evaluation of antifungal. It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. Molecular iodine catalyses a benzylic sp 3 ch bond amination of 2aminobenzaldehydes and 2aminobenzophenones with benzylamines to provide quinazolines in very good yields. Synthesis and anticancer activity of new quinazoline. Jun 25, 2015 general procedure for the synthesis of quinazoline schiff bases. In alkaline medium, where the anhydrous neutral species of quinazoline were predominantly undergo oxidation with kmno 4 furnished a high yield of 3,4dihydro4oxo quinazoline was also formed. Novel ferrocene conjugates of tricyclic quinazoline derivatives are prepared by condensation of active c. It is a light yellow crystalline solid that is soluble in water. Synthesis, quinazolines, piperazines, characterization, anticonvulsant activity. Synthesis and biological evaluation of quinazoline4thiones by lenka kubicova 1, martin sustr 1, katarina kralova 2, vladimir chobot 1, jitka vytlacilova 1, ludek jahodar 1, pia vuorela 3, milos machacek 1 and jarmila kaustova 4. Name reactions name reactions and reagents in organic. Synthesis of porous covalent quinazoline networks cqns and.
Synthesis, characterization, and anticancer activity of new. Theoretical considerations show that the expected order of reactivity is. Coppercatalyzed synthesis of quinazoline derivatives via. Original article cesium carbonate catalyzed efficient synthesis of quinazoline2,41h,3hdiones using carbon dioxide and 2aminobenzonitriles yogesh p. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Reaction of 5aminotetrazole triethylammonium salt and 2fluoro6chlorobenzaldehyde resulted in the formation of 6chlorotetrazolo1,5aquinazoline instead of the expected azomethine. Synthesis and antimicrobial activity of some new quinazoline derivatives dhaval j. Cedira nib azd2171 shown in figure 1e, on the other hand, is an example of an nunsubstituted indoleether quinazoline hybrid that has been found to be a highly potent, orally bioavailable and selective vascular endothelial growth factor receptor vegfr inhibitor for the treatment of cancer,14. Seasonal variation of vasicine212 content in various parts of the plant inflorescence, leaf, petiole, root, and stem bark used in traditional medicine was studied by arambewela and coworkers in an attempt to determine the.
Hydrogenation of the obtained quinazoline afforded 6chloro4,5dihydrotetrazolo1,5aquinazoline. Synthesis and biological evaluation of quinazoline 4thiones article pdf available in molecules 811. Synthesis of some novel quinazoline derivatives having anticancer activity. Design, synthesis and biological evaluation of spiro. Synthesis and functionalization of novel quinazoline.
Devi and coworkers have reported the synthesis of some new aza isatin derivatives containing 43h quinazolinones. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. Novel series of spiro2h,3hquinazoline2,1cyclohexane derivatives ixvi were synthesized and biologically evaluated as cytotoxic agents against human breast carcinoma cell lines mcf7 using doxorubicin as a reference drug. The 12aminophenylethanone was reacted with hcl gas in anhydrous condition we get hydrochloride salt of 1. A new and facile synthesis of quinazoline2,41h,3hdiones. Chemical characteristics, synthetic methods, and biological. The excess of acetic anhydride was removed by distillation under reduced pressure. Research article synthesis, characterization, and anticancer. Unlimited viewing of the articlechapter pdf and any associated supplements and figures. Oxidation catalytic hydrogenation of quinazoline stopped. Mar 25, 2020 a series of sulphonyl acetamide analogues were generated on the quinazoline ring through a multistep reaction starting from 2mercapto3hquinazolin4one. New efficient synthesis of imidazo2,1bquinazoline2,5. The research on biological activity of quinazoline compounds started when the compound 2methyl1,3aryl4 quinazoline derivative was synthesized. A more satisfactory synthesis of quinazoline was subsequently devised by gabriel in 1903.
Ashour2 1department of pharmaceutical chemistry, college of pharmacy, alkharj university, saudi arabia and 2department of. Design, synthesis and preliminary pharmacological screening antimicrobial, analgesic and antiinflammatory activity of some novel quinazoline derivatives biswajit dash 1, suvakanta dash, damiki laloo, chitrani medhi2 1girijananda chowdhury institute of pharmaceutical science, azara, hathkhowapara, guwahati781017, assam, india. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. The quinazoline alkaloid vasicine212 is the major alkaloid oiadhatoda vasica l. Quinazoline derivatives are well known to have a diverse array of therapeutic activities. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution.
A simple and highly efficient process for synthesis of. The nhexyl substituted isatinquinazoline derivative has been found to be relatively active against screened gram positive, gram negative bacteria and fungi species in comparison to other compounds fig. Synthesis of quinazoline and quinazolinone derivatives via ligandpromoted rutheniumcatalyzed dehydrogenative and deaminative coupling reaction of 2aminophenyl ketones and 2aminobenzamides with amines. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Quinazoline alkaloid an overview sciencedirect topics. Synthesis of some new quinazolinone derivatives and. General procedure for the synthesis of quinazoline schiff bases. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line.
Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolines. Typical quinazoline alkaloids include arborine, glomerin, homoglomerin, glycorine, glycosminine, febrifugine, and vasicine figure 2. Synthesis of quinazoline and quinazolinone derivatives via. Design, synthesis and biological evaluation of novel quinazoline derivatives as potential anticancer agents ahmed m. The synthesis of some quinazoline derivatives and their. Pdf synthesis and biological evaluation of quinazoline4.
According to the main method the authors adopted in their research design, those synthetic methods were divided. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. The gibson synthesis scheme i starts from 6,7dimethoxy quinazoline4one, which is demethylated using lmethionine and methanesulfonic acid, protected with acetyl group and converted into chloramine derivative, followed by coupling with 3chloro4fluoro aniline. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Recently, many efforts have been focused by chemists on the modification of quinazoline ring for development of pharmaceutical and clinical compounds.
We synthesized disubstituted quinazoline derivatives using various synthetic routes and evaluated their biological activities to identify new biologically active pharmacophores that may be specifically applied as antibacterial agents. Synthesis of some novel quinazoline derivatives having. The fact that a certain chemical substance is restricted to a specific function, such as sex attraction, does not necessarily mean that it was evolved. Acanthaceae, a plant reputed to be used in many ayurvedic medicinal preparations. Nitration is the only known electrophilic substitution reaction of quinazoline. Synthesis of 1hquinazoline4ones using intramolecular. New efficient synthesis of imidazo2,1bquinazoline2,51h,3hdiones via a consecutive azawittigheterocumulenemediated annulation. Evaluation of these compounds against different cell lines identified compounds 7 and 17 as most active anticancer agents as they showed effectiveness on the four tested cell lines. Synthesis, characterization, and anticancer activity of. Design, synthesis and biological evaluation of novel. Synthesis of some novel quinazoline derivatives having anti. Synthesis and biological evaluation of quinazoline4thiones article pdf available in molecules 811. Research article synthesis, characterization, and anticancer activity of new quinazoline derivatives against mcf7 cells fadhillaftafaraj, 1,2 maryamzahedifard, 3 mohammadjavadpaydar, 4.
The library of synthesised analogues was screened for in vitro cytotoxic activity against various human cancer cell lines such as hct1 and ht15 colon, mcf7breast, pc3 prostrate, sf268 cns using mtt method. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. Synthesis of 23chloropropyl4hbenzod 1, 3 oxazin4one 3 compound 2 0. Synthesis, biological evaluation and molecular docking of. Synthesis, characterization and evaluation of antifungal and. The preparation of the quinazoline came many years later when bischler and lang obtained it by decarboxylation of the 2carboxy derivative. For synthesis of quinazoline derivatives we have used piperazine, aminoethan1ol, ptoluidine and pchloroaniline because individually they shows important pharmacological and other activities therefore at the time of synthesis we expected that after synthesis of these quinazoline derivatives they will be show some. Synthesis of 14oxo2arylquinazolin34hyl urea from 2aryl3amino43h quinazolinone. An acceptorless coupling of oaminobenzamides with methanol has been accomplished in the presence of the metalligand bifunctional catalyst cpir2,2. Alkylation and hydrazinolysis of the inherent thioxo group in afforded the corresponding thioethers 423 and hydrazine derivatives.
Synthesis of 6chlorotetrazolo1,5 a quinazoline and 6. Review article chemical characteristics, synthetic methods. The residue was cooled and the product crystallized. The use of oxygen as an oxidant combined with the transitionmetal, additive and solvent. Quinazoline in 1905 riedel obtained a patent describing a synthesis of quinazoline from onitrobenzaldehyde through reaction with formamide to the onitrobenzylidenediformamide. It is the basic structural unit of pharmaceuticals and plays an important role in modern synthesis of antitumor drugs. First, the reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. As literature serve the synthesis 2chloromethyl4methylquinazoline derivatives synthesis by the process 8. Then, cyclization of the urea derivatives with naoh afforded the monosodium salts of. Review article chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives mohammadasif department of pharmacy, grd pg institute of management and technology, dehradun, uttarakhand, india. Synthesis and anticancer activity of new quinazoline derivatives. Application quinazoline was used to study the electrochemical behaviour of quinazoline using modern polarographic and voltammetric methods.
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