If the inline pdf is not rendering correctly, you can download the. A variety of c1 sources could be used, affording 4. The synthesis of known quinazoline heterocycles by conventional ways is a hard work that implies many synthetic steps and expensive starting materials, and. Solventcatalystfree microwaveassisted synthesis of quinazolines. Our catalyst has been found to be almost equally effective in quinazoline synthesis via c. The synthesis of a series of pushpull arylvinyl styryl, aryl, and arylethynyl quinazoline derivatives by means of different straightforward protocols is reported. Synthesis and biological evaluation of quinazoline4thiones.
Synthesis, molecular modeling and anti cancer evaluation of a series of quinazoline derivatives. Synthesis of porous covalent quinazoline networks cqns. Hydrogenation of the obtained quinazoline afforded 6chloro4,5dihydrotetrazolo1,5aquinazoline. The data from antibacterial examinations indicated that the substituent on the phenyl ring exerted significant influence on the antibacterial. An efficient cucatalyzed synthesis of quinazolines via the cn bond formation reactions between nh bonds of amidines and csp3h bonds adjacent to sulfur or nitrogen atoms in the commonly used solvents, such as dmso, dmf, dma, nmp or tmeda, followed by intramolecular cc bond formation reactions was devel. 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. Synthesis, molecular modeling and anticancer evaluation of a. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. Reaction of 5aminotetrazole triethylammonium salt and 2fluoro6chlorobenzaldehyde resulted in the formation of 6chlorotetrazolo1,5aquinazoline instead of the expected azomethine. Reactions of organolithium reagents with quinazoline. Synthesis of some new quinazolinone derivatives and. Quinazoline derivatives are one of the most important sixmembered nitrogencontaining heterocyclic compounds as many naturally occurring and pharmaceutical compounds contain quinazoline moiety as the core unit.
In contrast to quinazolidine2,4dione synthesis using 2methoxycarbonyl phenylisocyanate, 3 b intermediate 5 smoothly cyclized without subsequent base treatment to give quinazoline2thioxo4one 6. Synthesis and reactivity of some novel quinazoline. Znmediated reduced synthesis of quinazoline derivatives. It has been used for the treatment of high blood pressure as adrenergic blockers, anxiety, and panic disorder prazosin and has also been found useful for epidermal growth factor. Synthesis and characterization of quinazoline derivatives. Synthesis, characterization, and anticancer activity of. Pdf owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities. The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. Synthesis and screening of some new fluorinated quinazolinone. Synthesis of chalcone incorporated quinazoline derivatives.
Co 2 involved synthesis of quinazoline2,41h,3hdiones in water using melamine as a thermoregulated catalyst. The catalytic coupling method provides an efficient synthesis of. Coppercatalyzed annulation of amidines for quinazoline. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolinones. The nature of the oxidant exhibited a considerable effect on the reaction, and tert. Center of organic and pharmaceutical chemistry, national academy of.
It has been applied to substitute quinozolines, for the preparation of 6,7dimethoxy quinazoline through the intermediate 6nitroveratradehyde. The use of oxygen as an oxidant combined with the transitionmetal, additive and solvent. The research on biological activity of quinazoline compounds started when the compound 2methyl1,3aryl4quinazoline derivative was synthesized. Synthesis and anticancer activity of new quinazoline. Synthesis, anticancer and antimicrobial characterization of some novel quinazoline derivatives. 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. Herein, we introduce for the first time the synthesis of covalent quinazoline networks cqns using an ionothermal synthesis protocol. 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. Quinazoline and quinazolinone are reported for their diversified biological activities and compounds with different substitutions bring together to knowledge of a target with understanding of the molecule types that might. The usual synthesis of quinazolines make use of an odisubstituted benzene structure from which the quinozoline. The first total syntheses of verrucines a and b and anacine revised structure were accomplished on sasrin resin. Guoying zhao, a lingling mu, a b latif ullah, a meng wang, a hongping li, b xinxin guan b a beijing key laboratory of ionic liquids clean process, state key laboratory of multiphase complex systems, key laboratory of. It is a light yellow crystalline solid that is soluble in water.
Stephen j baker, steven m firestine, david smithrud, frank salinas, stephen j benkovic. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Unfortunately, classic chemical synthesis does not provide an opportunity for the formation of n. Quinazoline alkaloid an overview sciencedirect topics. Pdf synthesis of some new quinazolinone derivatives and.
Quinazolinones benzopyrimidine derivatives, are compounds with wide spectrum of biological activities, including. Efficient solidphase synthesis of quinazoline2thioxo4. With an objective to synthesize compounds with high anticancer and other antimicrobial properties, a systematically planned organic synthesis was carried out. Synthesis and evaluation of some new 4, 6 disubstituted quinazoline derivatives for antimicrobial and antifungal activities chavan b. Acanthaceae, a plant reputed to be used in many ayurvedic medicinal preparations. General reaction scheme for the synthesis of the target compounds 4, 5 and 6. Chemical characteristics, synthetic methods, and biological.
The deaminative coupling reaction of 2aminobenzamides with amines led to the efficient formation of quinazolinone products. It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. Solventcatalystfree microwave assisted synthesis of quinazolines. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Co2 involved synthesis of quinazoline2,41h,3hdiones in.
In contrast to quinazolidine2,4dione synthesis using 2methoxycarbonyl phenylisocyanate, 3 b intermediate 5 smoothly cyclized without subsequent base treatment to give quinazoline 2thioxo4one 6. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. Download fulltext pdf synthesis, biological evaluation and molecular docking of pyrimidine and quinazoline derivatives of 1,5benzodiazepine as potential anticancer agents. The invention concerns quinazoline derivatives of formula i. Pdf synthesis and biological evaluation of quinazoline4. Synthesis and evaluation of some new 4, 6 disubstituted. Synthesis and antimicrobial activity of some quinazolinone. An oxidant, base and metal free methodology has been developed for the synthesis of various 2substituted and nonsubstituted benzazoles, quinazolines and quinazolinones using oxalicmalonic acids as an in situ carbon source.
View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Coppercatalyzed synthesis of quinazoline derivatives via. Intrinsic catalytic activity of an acidic ionic liquid as. The whole reaction sequence runs without isolation of intermediates and most importantly, without the need of perfluorinated solvents. Abstractto explore the pharmacological and structureactivity relationship of a series of nsubstituted4oxo2substitutedphenylquinazolin34hyl, substituted benzene sulfonamide derivatives 125 were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. This methodology is applicable for a wide range of substituted ophenylenediamine, oaminothiophenol, oaminophenol and oaminobenzamide containing various.
Synthesis, anticancer and antimicrobial characterization. Synthesis of 6chlorotetrazolo1,5 a quinazoline and 6. The salkylated and s glycosylated of quinazoline derivatives were synthesized. Synthesis of two bifunctional ligands for the quest threehybrid system. Download fulltext pdf quinazolinone and quinazoline derivatives. The in situ formed ruthenium catalytic system rul was found to be highly selective for the dehydrogenative coupling reaction of 2aminophenyl ketones with amines to form quinazoline products. Highly efficient, one pot, solvent and catalyst, free synthesis of. Synthesis of some novel quinazoline derivatives having anticancer activity. Synthesis of some novel quinazoline derivatives having.
Merits of this reaction are selfcatalysis, easy workup process, less reaction time, and environmental friendliness. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. Total solid phase syntheses of the quinazoline alkaloids. Quinazoline derivatives with antitubercular activity. The preparation of arylvinylquinazolines was performed by aldol condensation of the appropriate methylquinazoline and functionalized benzaldehyde. Synthesis of 4arylaminoquinazoline2carboxylic acid derivatives. General experimental procedure for the synthesis of 8. They explored the optimal reagent, volume and heating temperature by testing different reagents under different reaction time and temperature. Pdf is not rendering correctly, you can download the pdf file here. This study was focused on the synthesis of novel quinazolinone derivatives and the study of vasorelaxant effects of 3substituted 2methyl quinazoline43hones. Albayati and others published novel quinazolinone derivatives.
This work confirmed the structure of verrucine a and unambiguously showed verrucine b to be a derivative of dphenylalanine and lglutamine. The study also proved that anacine and its epimer are quinazoline alkaloids, not benzodiazepines as originally proposed. Synthesis of quinazoline and quinazolinone derivatives via. The photophysical properties of the compounds are described. Pdf wide range of quinazolinone biological properties including. Unfortunately, synthetic methods for quinazoline derivatives are not. Synthesis of 4arylaminoquinazoline2carboxylic acid derivatives by the. Facile access to potent antiviral quinazoline heterocycles. The quinazoline alkaloid vasicine212 is the major alkaloid oiadhatoda vasica l. Ep 1667992 b1 quinazoline derivatives the lens free.
However, cleavage of the products with 95% tfah 2 o gave a mixture of 7 and 8. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Synthesis and antimicrobial activity of some quinazolinone derivatives. Quinazoline derivatives are well known to have a diverse array of therapeutic activities. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. Quinazolines are nitrogen containing heterocyclic scaffolds and have showed a wide range biological activities, such as anticancer connell, 2004. Synthesis, quinazolines, piperazines, characterization, anticonvulsant activity. Synthesis and photophysical studies of a series of. Synthesis and antimicrobial activity find, read and cite all the research you need on researchgate. Pdf synthesis, biological evaluation and molecular.
Several biological activities were reported for fused tricyclic quinazoline derivatives 8, 9 among which deoxyvasicinone is highly interesting and has been. Recent structures with potent anticancer activity chapter pdf available february 2018 with 55 reads. A greener approach for the synthesis of quinazoline intermediates using an ionic liquid was developed where the ionic liquid is used as an intrinsic reaction catalyst and a solvent. Molecular iodine catalyses a benzylic sp 3 ch bond amination of 2aminobenzaldehydes and 2aminobenzophenones with benzylamines to provide quinazolines in very good yields. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolines.