Synthesis and evaluation of some new 4, 6 disubstituted. In one of our previous works we described the total synthesis of derivatives of quinazolinone by interaction of amides of anthranilic acid with appropriate aldehydes. Microwavepromoted synthesis of ssubstituted quinazoline. Novel threestep synthesis of imidazo1,2cquinazoline56h. Synthesis, characterization and evaluation of antifungal and. Novel synthesis of quinazoline derivatives from 2 nitrobenzaldehyde or 2nitrophenyl ketones with. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. In this paper, we report the synthesis of nsubstituted3nitrophthalimide derivatives iiiii, the reactions of phthalimide iii with amines, hydrazines, and amino acid derivatives to synthesise a small library of 3substituted5.
Synthesis of new 4 3h quinazolinone derivatives under solventfree conditions using peg400 palle v. Uses of 2ethoxy43h quinazolinone in synthesis of quinazoline and quinazolinone derivatives of antimicrobial activity. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. The molecular structure of the synthesized imidazobenzimidazo1,2c quinazoline derivatives. Synthesis and properties of quinazoline derivatives. Quinazoline derivative, synthesis, bioactivity introduction quinazoline derivatives, which belong to the ncontaining heterocyclic compounds, have caused universal concerns due to their widely and distinct biopharmaceutical activities. Synthesis of quinazoline derivatives containing veratrole. Synthesis of new 4 3h quinazolinone derivatives using 54h oxazolones. Two series of 2phenyl43h quinazolinone derivatives have been. 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. Quinazolinone and quinazoline derivatives semantic scholar.
Catalystfree synthesis of quinazoline derivatives using. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives. Synthesis of new 43hquinazolinone derivatives using 54h. Synthesis and evaluation of antioxidant properties of some. According to the main method the authors adopted in their research design, those synthetic methods were divided. The journal of organic chemistry 2010, 75 22, 79367938. Pdf synthesis and evaluation of quinazoline amino acid. Synthesis and biological evaluation of quinazoline. Files available from the acs website may be downloaded for. Medicinal chemists synthesized a variety of quinazoline compounds with different biological activities by installing various active groups to the. All steps were carried out under easy and userfriendly. A novel synthesis of iimidazo1,2c quinazoline 56hthione framework was developed through a threestep reaction starting from benzil.
Five trisubstituted quinazolones and eight trisubstituted quinazoline 4thiones have been tested for antibacterial effects by a microdilution method. Design, synthesis, characterization and antimicrobial. Coppercatalyzed synthesis of quinazoline derivatives via. Starch sulfate as biosupported solid acid catalyst was applied to synthesis of heterocyclic compounds such as 2,3dihydroquinazolin41hone, 2substituted1,2,3,4tetrahydro4quinazolinones, 12aryl8,9,10,12tetrahydrobenzoaxanthen11one, 1,8dioxooctahydroxanthenes, and 5hdibenzob,ixanthene5,7,12,14htetraone derivatives under thermal solventfree conditions.
Facile synthesis of 3substituted quinazoline2,4dione and 2. Synthesis of quinazoline derivatives seventysix original quinazoline derivatives were synthesized. Synthesis of quinazoline and quinazolinone derivatives via. Synthesis and evaluation of new polysubstituted quinazoline derivatives as potential antimicrobial agents, pharma chem. Synthesis of some novel quinazoline derivatives having anticancer activity. Design, synthesis, antiproliferative activity and docking. Synthesis and thermal decomposition kinetics of some pyrazolo. Synthesis of quinazoline derivatives containing veratrole and. Synthesis of some new quinazolinone derivatives and. The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. Pdf owing to the significant biological activities, quinazoline derivatives. Under the guidance of our previous work, we synthesized 21 new structures of quinazolines 3a3u and evaluated their in vitro anticancer activity against a549, hct116 and mcf7 cell lines using the mtt method.
Chemical characteristics, synthetic methods, and biological. Design, synthesis and antiinfluenza a virus activity of. Pdf uses of 2ethoxy43h quinazolinone in synthesis of. Synthesis of some novel quinazoline derivatives having anti. The action of alkylating agents on 12 carboxyethyl1h,3h quinazoline2,4dione was utilized to synthesize corresponding esters. Catalystfree synthesis of quinazoline derivatives using low.
Synthesis and thermal decomposition kinetics of some pyrazolo quinazoline derivatives shipra baluja, paras ramavat, kajal nandha physical chemistry laboratory, department of chemistry, saurashtra university, rajkot 360005, gujarat, india email address. If you do not see its contents the file may be temporarily unavailable at the journal website or you do not have a pdf plugin installed and enabled in your browser. These derivatives were obtained by the reaction of different biphenyl compounds 5 and the corresponding substituted 3hquinazoline4thiones, obtained by conventional chemistry and described methods. Oct 01, 2004 read synthesis of new quinazoline derivatives, heterocyclic communications on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. A series of tetrahydrotetrazolo1,5a quinazoline derivatives were prepared by the threecomponent condensation reaction of 5aminotetrazole 5at, benzaldehydes, and dimedone in the presence of ptoluenesulfonic acid ptsa as a solid acid catalyst under solventfree conditions. Synthesis of 23chloropropyl4hbenzod 1, 3 oxazin4one 3 compound 2 0. Quinazoline is an organic compound with the formula c 8 h 6 n 2. The 12aminophenylethanone was reacted with hcl gas in anhydrous condition we get hydrochloride salt of 1. 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. We have developed a general and highly efficient coppercatalyzed method for synthesis of quinazoline and quinazolinone derivatives, the target products were obtained in good to excellent yields via cascade reactions of amidine hydrochlorides with substituted 2halobenzaldehydes, 2halophenylketones, or meth. Methods for the synthesis of quinazoline and quinazolinone derivatives benzoylene urea some methods were reported for the synthesis of quinazolines and quinazolinones are as follows.
Synthesis and thermal decomposition kinetics of some. Synthesis and reactivity of some novel quinazoline derivatives. Synthesis and evaluation of some new 4, 6 disubstituted quinazoline derivatives for antimicrobial and antifungal activities chavan b. The retrosynthetic pathway for the biphenyl substituted thioquinazoline derivatives 14 is shown in scheme 1. Anticancer evaluation, quinazoline derivatives, synthesis. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Six series of quinazoline derivatives bearing oxazole or imidazole 8af, 9af, 10ad, 11af, 12ad and ai were designed, synthesized and their ic 50 values evaluated against three cancer cell lines a549, mcf7 and pc3. Synthesis, characterization, and anticancer activity of. Synthesis of 2chloromethyl quinazoline 5a5ithe reaction of. Sep 28, 2006 coppercatalyzed synthesis of quinazoline derivatives via ullmanntype coupling and aerobic oxidation. Synthesis of quinazoline and quinazolinone derivatives via ligandpromoted rutheniumcatalyzed dehydrogenative and deaminative coupling reaction of 2aminophenyl ketones and 2aminobenzamides with amines.
A total of 22 quinazoline thioether derivatives incorporating a 1,2,4triazolo4,3apyridine moiety were designed, synthesized, and evaluated as antimicrobial agents in agriculture. Reduction of this with zinc and dilute acetic acid gave quinozoline in good yield. Synthesis and biological evaluation of quinazoline4thiones. Novel threestep synthesis of imidazo1,2cquinazoline5. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Coppercatalyzed synthesis of quinazoline derivatives via ullmanntype coupling and aerobic oxidation chen wang, shangfu li, hongxia liu, yuyang jiang and hua fu key laboratory of bioorganic phosphorus chemistry and chemical biology ministry of education, department of chemistry, tsinghua university, beijing 84, peoples republic of. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. The biological activities of the synthesized quinazoline derivatives also are discussed. Synthesis and antimicrobial activity of some new quinazoline. Pdf synthesis and anticancer activity of new quinazoline. Introduction quinazoline 43hone ring system has been consistently regarded as promising privileged structural icon ow ing to its pharmacodynamic versatility in many of its synthetic derivatives as well as in several naturally occur. The synthesis of new quinazoline derivatives with 2,3 and 4positioned cymantrenyl fragment is described.
A variety of c1 sources could be used, affording 4. Medical college, thiruvananthapuram, kerala, pin696011, india. Oct 17, 2012 3substituted quinazoline2,41h,3hdione and 2,3disubstituted quinazolineone derivatives attract considerable interest due to their pharmacological properties. Applying this methodology in present work, 6ahisoindolo2,3a quinazoline 5,11diones and their 6hydroxyanalogues were synthesized by the interaction of anthranilamides and 2aminonhydroxybenzamides with 2formyl. Synthesis and anticancer activity of new quinazoline. An efficient synthesis of quinazoline and xanthene. The hydrolysis and hydrazinolysis of the last were accomplished. Quinazoline pharmacophore in therapeutic medicine covenant. This protocol provides a simple onestep procedure with the advantages of easy workup, mild reaction conditions.
Highly efficient, one pot, solvent and catalyst, free synthesis of. Synthesis, characterization and apoptotic activity of. Ho wev er, none of the synthesiz ed compounds w ere super ior to the standar d ofloxacin table2. Synthesis, characterization, and anticancer activity of new quinazoline derivatives against mcf7 cells fadhil lafta faraj, 1, 2 maryam zahedifard, 3 mohammadjavad paydar, 4 chung yeng looi, 4 nazia abdul majid, 3 hapipah mohd ali, 1 noraini ahmad, 1 nura suleiman gwaram, 1 and mahmood ameen abdulla 5. Most compounds showed good to excellent anticancer activity.
The excess of acetic anhydride was removed by distillation under reduced pressure. Synthesis of new quinazoline derivatives, heterocyclic. A novel, rapid and efficient microwaveassisted synthesis of ssubstituted quinazoline derivatives was obtained using 1,4dihydroquinazoline2thiol and various boronic acids with copper catalyst in onepot reactions. The resulting 2nitrophenyl4,5diphenyl1himidazole from the reaction of benzil and different 2nitrobenzaldehyde, reduction of nitro group and then cyclization reaction with carbon disulfide cs2. All quinazoline derivatives showed significant antibacterial activity against tested pathogens. As literature serve the synthesis 2chloromethyl4methylquinazoline derivatives synthesis by the process 8. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. Thus, we designed and synthesized a series of 2,4disubstitued quinazoline derivatives and evaluated their antiiav activity in this study, aiming at finding new quinazoline derivatives with potent antiiav activity and facilitate the further development of these compounds. Alkylation and hydrazinolysis of the inherent thioxo group in afforded the corresponding thioethers 423 and hydrazine derivatives. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. Unexpected coppercatalyzed cascade synthesis of quinazoline. Among these compounds, the chemical structure of compound 6l was further confirmed via singlecrystal xray diffraction analysis.
Elseginy3 1department of pharmaceutical chemistry, faculty of pharmacy, cairo university, egypt. Reddys laboratories, bachupalli, hyderabad, india, 500 072 bdepartment of chemistry, college of engineering. The nature of the oxidant exhibited a considerable effect on the reaction, and tert. A rhiicatalyzed transannulation of nsulfonyl1,2,3triazoles with 2,1benzisoxazoles provides quinazoline derivatives.
Research article synthesis, characterization, and anticancer activity of new quinazoline derivatives against mcf7 cells fadhillaftafaraj, 1,2 maryamzahedifard, 3 mohammadjavadpaydar, 4 chungyenglooi, 4 naziaabdulmajid, 3 hapipahmohdali, 1 norainiahmad, 1 nurasuleimangwaram, 1 andmahmoodameenabdulla 5 department of chemistry, faculty of science, university of malaya. Synthesis of quinazoline and quinazolinone derivatives. Oxidation catalytic hydrogenation of quinazoline stopped. It is a light yellow crystalline solid that is soluble in water. All compounds were saved as pdbqt format and docking with autodock vina was. 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.
Jan 24, 2007 the invention concerns quinazoline derivatives of formula i. Synthesis and anticancer activity of new quinazoline derivatives article pdf available in saudi pharmaceutical journal 257 april 2017 with 391 reads how we measure reads. Synthesis of some novel quinazoline derivatives having. Though the parent quinazoline molecule is rarely mentioned by itself in technical literature, substituted derivatives have been synthesized for medicinal purposes such as antimalarial and anticancer agents. Scmnps are easy purification, reusability of the catalyst, good yields of products with short time reactions. Synthesis of chalcone incorporated quinazoline derivatives as anticancer agents article pdf available in saudi pharmaceutical journal 252.
When the effervescence ceased, the precipitate obtained was filtered and washed with water. Synthesis and evaluation of quinazoline amino acid derivatives as mono amine oxidase mao inhibitors. Synthesis of quinazoline derivatives and their biological activities. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. Synthesis of 1 4oxo2arylquinazolin3 4hyl urea from 2aryl3amino43h quinazolinone. From anthranilic acid and urea the fusion of anthranilic acid with urea gave 1,2,3,4tetrahydro2,4dioxoquinazoline see scheme 14. Potential of quinazoline and quinazolinone derivatives. Synthesis and antimicrobial activity of some new quinazoline derivatives dhaval j. Polyphosphoric acid effected the conversion of 12carboxyethylquinazolinedione to 1,3,7trioxopyrido1,2,3k,jquinazoline. Synthesis and evaluation of quinazoline derivatives as.
Most of the thirtyfive target compounds showed excellent antiproliferative activity against one or several cancer cell lines. 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. It is the basic structural unit of pharmaceuticals and plays an important role in modern synthesis of antitumor drugs. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. 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. Alkylation of 2substituted quinazolin4ones with cymantrenylalkyl bromides on using k 2 co 3, potassium tertbutoxide, and sodium hydride as bases has been studied. Synthesis of new 43hquinazolinone derivatives under.
Synthesis of quinazoline derivatives catalyzed by a new efficient reusable nanomagnetic catalyst supported with functionalized piperidinium benzene. This study was focused on the synthesis of novel quinazolinone derivatives and the study of vasorelaxant effects of 3substituted 2methyl quinazoline43h ones. Highly efficient coppercatalyzed cascade synthesis of. Some novel quinazoline derivatives are prepared via one. Novel ferrocene conjugates of tricyclic quinazoline derivatives are prepared by condensation of active c. Design, synthesis, characterization and antimicrobial evaluation of novel 2,4disubstituted quinazoline derivatives anant n deshpande1 and shashikant c dhawale2 1department of pharmaceutical chemistry, government college of pharmacy, vidya nagar, karad, maharashtra, india. Shakhidoyatov chemistry of heterocyclic compounds volume 35, pages 821 824 1999cite this article. Ep 1667992 b1 quinazoline derivatives the lens free. The deaminative coupling reaction of 2aminobenzamides with amines led to the efficient formation of quinazolinone products. Synthesis and antibacterial activity of quinazoline derivatives.
Synthesis of new quinazolinecontaining hydroxamic acids. Design and synthesis of imidazobenzimidazo 1, 2c quinazoline. Synthesis of chalcone incorporated quinazoline derivatives. Application quinazoline was used to study the electrochemical behaviour of quinazoline using modern polarographic and voltammetric methods. Pdf on dec, 2019, satyendra mishra and others published quinazolinone and. Oxidation catalytic hydrogenation of quinazoline stopped after the absorption of one molecules of hydrogen and.
Synthesis of quinazoline derivatives catalyzed by a new. The synthesis of quinazoline derivatives has attracted the attention of chemists and has importance in medicinal chemistry because of the pharmacological applications for this heterocyclic ring system. Jun 03, 20 owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Efficient methods for synthesis of quinazolin4ones are e. Synthesis, characterization, and anticancer activity of new. Synthesis of bioactive quinazolin43hone derivatives. Utility of 2methylquinazolin43hone in the synthesis of. Antibacterial effects of trisubstituted quinazoline derivatives. Esihrms, and hplc purity spectra of compounds 8aa8gd pdf. Reactions of organolithium reagents with quinazoline derivatives. Synthesis of quinazoline derivatives containing veratrole and benzo15crown5 moieties. Reduction of this with zinc and dilute acetic acid gave quinozoline in. Routes for preparation of quinazoline 4thione derivatives can involve cyclization of a convenient precursor, thionation of the corresponding oxo analogs, or condensation reactions 25, 28, 37, 38.
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