Design, synthesis, characterization and antimicrobial. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. The cascade reaction includes a sequential ullmanntype coupling and aerobic oxidation and provides a convenient and practical strategy for the synthesis of. From anthranilic acid and urea the fusion of anthranilic acid with urea gave 1,2,3,4tetrahydro2,4dioxoquinazoline see scheme 14. To enhance egfr targeted therapies and ameliorate drug. Synthesis of some novel quinazoline derivatives having. Synthesis of quinazoline derivatives containing veratrole. Quinazoline in 1905 riedel obtained a patent describing a synthesis of quinazoline from onitrobenzaldehyde through reaction with formamide to the onitrobenzylidenediformamide. Antibacterial effects of trisubstituted quinazoline. According to the main method the authors adopted in their research design, those synthetic methods were divided. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride.
Synthesis of some novel quinazoline derivatives having anti. Synthesis of new 43hquinazolinone derivatives under. Synthesis and anticancer activity of new quinazoline derivatives. Synthesis, characterization and evaluation of antifungal. Synthesis of quinazoline derivatives containing veratrole and. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives.
Reduction of this with zinc and dilute acetic acid gave quinozoline in. 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. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. The heating of quinazoline iv in acetic anhydride or butan1ol gave quinazoline derivatives v or vi, respectively. 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. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Pdf synthesis and antimicrobial activity of some annelated. Solventcatalystfree microwaveassisted synthesis of quinazolines. Molecules free fulltext design, synthesis, and antitumor. Synthesis of new 4 3h quinazolinone derivatives under solventfree conditions using peg400 palle v. Quinazolines are nitrogen containing heterocyclic scaffolds and have showed a wide range biological activities, such as anticancer. Synthesis, characterization, and anticancer activity of new.
Synthesis of quinazoline derivatives containing veratrole and benzo15crown5 moieties. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. A variety of c1 sources could be used, affording 4. A simple and efficient, ligand free coppercatalyzed approach to quinazoline derivatives uses readily available substituted 2bromophenylmethylamines and amides as starting materials. 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 new synthesis of pyrrolo1,2c quinazoline from quinazolinium nylides. Solvent catalystfree microwaveassisted synthesis of quinazolines. Synthesis of some annelated quinazoline derivatives j. Review article chemical characteristics, synthetic methods. Design, synthesis and antiinfluenza a virus activity of. Synthesis and antimicrobial activity of some new quinazoline derivatives dhaval j. Quinazoline derivatives are well known to have a diverse array of therapeutic activities. Five trisubstituted quinazolones and eight trisubstituted quinazoline4thiones have been tested for antibacterial effects by a microdilution method.
Synthesis of some novel quinazoline derivatives having anticancer activity. 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. Green synthesis of substituted anilines and quinazolines. A series of c7substituted2morpholinonpyridin2ylmethylquinazolin4amine derivatives 3a3t were synthesized by using nickel catalyzed kumada cross coupling reaction.
A simple and efficient approach for the synthesis of 2aminoquinazoline derivatives in moderate to good yields. Synthesis and antimicrobial activity of some new quinazoline. Most compounds showed good to excellent anticancer activity. Synthesis and anticancer activity of new quinazoline. Efficient methods for synthesis of quinazolin4ones are e. 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. Alkylation and hydrazinolysis of the inherent thioxo group in afforded the corresponding thioethers 423 and hydrazine derivatives. The invention concerns quinazoline derivatives of formula i. 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. This reaction employs mild reaction conditions, is metal free and utilizes readily available starting materials making it a more viable reaction for scale up synthesis and ligand diversity. The nature of the oxidant exhibited a considerable effect on the reaction, and tert. Synthesis of 4arylaminoquinazoline2carboxylic acid derivatives.
The use of oxygen as an oxidant combined with the transitionmetal, additive and solvent. Some 5substituted 3aminopyrazoles were used for the synthesis of isoindolo2,1cpyrazolo1,5aquinazoline and pyrazolo5. Palladiumcatalyzed nmonoarylation of amidines and a onepot. Substituted quinazolines have been synthesized by a number of. These synthesized compounds were evaluated for antitumor. This reaction employs mild reaction conditions, is metalfree and utilizes readily available starting materials making it a more viable reaction for scale up synthesis and ligand diversity. Unfortunately, classic chemical synthesis does not provide an opportunity for the formation of n. Catalystfree synthesis of quinazoline derivatives using. Solventfree synthesis of isoindolo2,1cpyrazolo1,5a. 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. Synthesis and biological evaluation of quinazoline4thiones. Kumada cross coupling reaction for the synthesis of. Synthesis leading to novel 2,4,6trisubstituted quinazoline. 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 of some new quinazolinone derivatives and. Oxidation catalytic hydrogenation of quinazoline stopped after the absorption of one molecules of hydrogen and. Low melting mixture of maltosedimethylurea dmunh4cl was found to be an inexpensive, nontoxic, easily biodegradable and effective reaction medium in the catalystfree synthesis of quinazoline derivatives. Methoxyl, methyl, halogen, and trifluoromethyl groups on stilbeneamino were detected. Unfortunately, synthetic methods for quinazoline derivatives are not general. Chemical characteristics, synthetic methods, and biological. Synthesis, characterization, and anticancer activity of. Potential of quinazoline and quinazolinone derivatives. Synthesis, characterization and evaluation of antifungal and.
The biological results showed that most of quinazoline derivatives exhibited potent antiproliferative activities against a panel of three tumor cell lines and a good inhibitory effect against the adhesion and migration of human umbilical vein endothelial cells huvecs. Design, synthesis and biological evaluation of spiro. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts. Synthesis and biological evaluation of quinazoline. Quinazoline is a bicyclic compound earlier known as benzo 1, 3diazine was prepared in the laboratory by gabriel in 1903. A few examples of quinazoline ring synthesis by ring contraction have also been reported. A series of novel 2,4,6trisubstituted quinazoline derivatives 6 have been synthesized from anthranilic acids 1 in five steps via. A new synthesis of pyrrolo1,2cquinazoline from quinazolinium nylides. Molecular iodine catalyses a benzylic sp 3 ch bond amination of 2aminobenzaldehydes and 2aminobenzophenones with benzylamines to provide quinazolines in very good yields.
Pdf a highly efficient and versatile synthetic approach to the synthesis of. 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. Palladiumcatalyzed nmonoarylation of amidines and a one. Reduction of this with zinc and dilute acetic acid gave quinozoline in good yield. By 1980, about 50 kinds of derivatives of this class with different medicinal and. A method for the pdcatalyzed narylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. In an attempt to explore a new class of epidermal growth factor receptor egfr inhibitors, novel 4stilbenylamino quinazoline derivatives were synthesized through a dimorth rearrangement reaction and characterized via ir, 1 hnmr, cnmr, and hrms.
Studies on molecular mechanisms demonstrated that it can induce the s phase cell cycle arrest and cell apoptosis in hepg2 cells. Marvania et al3 synthesized a series of phenyl n mustardquinazoline derivatives and. Catalystfree synthesis of quinazoline derivatives using low. Anticancer evaluation, quinazoline derivatives, synthesis. Routes for preparation of quinazoline4thione derivatives can involve cyclization of a convenient precursor, thionation of the corresponding oxo analogs, or condensation reactions 25, 28, 37, 38. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Synthesis of new quinazoline derivatives, heterocyclic. All the target compounds were characterized and tested for their antibacterial activity against gram. Synthesis, characterization and apoptotic activity of quinazolinone schiff base derivatives toward mcf7 cells via intrinsic and extrinsic. It also discloses a method of treating an angiogenesisrelated disorder with one of these compounds. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolines. Development of a series of novel 4anlinoquinazoline. Synthesis of quinazoline and quinazolinone derivatives via.
The structure of the key intermediate 2 was assigned using 2d cosy and 2d noesy correlation spectrum. Synthesis of chalcone incorporated quinazoline derivatives as. Anthranilic acid derivatives 2 and 7 with a free carboxylic acid and chlorine atom at the end of side chain. Jun 03, 20 owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. The deaminative coupling reaction of 2aminobenzamides with amines led to the efficient formation of quinazolinone products. Synthesis, characterization and apoptotic activity of. In addition to supporting the proposed iaa mechanism, we also showed for the first time how phthalimides, used in the synthesis of quinazoline 5acid derivatives from an isatin derivative, are. Shakhidoyatov chemistry of heterocyclic compounds volume 35, pages 821 824 1999cite this article. In an attempt to explore a new class of epidermal growth factor receptor egfr inhibitors, novel 4stilbenylamino quinazoline derivatives were synthesized through a dimorth rearrangement reaction and characterized via ir, 1hnmr, cnmr, and hrms. We now wish to report here in synthesis of several newer derivatives of quinazolinones by. Based on linagliptin, this study discusses the design, synthesis and biological evaluation of spiro cyclohexane1,2quinazoline scaffold hybridized with various heterocyclic ring systems through different atomic spacers as a highly potent dpp4 inhibitors.
The cyclisation of thiourea ii was achieved using acetic anhydride to form quinazoline derivative iv. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. Design, synthesis and antiinfluenza a virus activity of novel 2,4disubstituted quinazoline derivatives. Synthesis and evaluation of 2,4disubstituted quinazoline. The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. Green synthesis of substituted anilines and quinazolines from. Synthesis of quinazoline derivatives containing veratrole cf.
Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. 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. The synthetic studies of the quinazoline derivatives discussed in this section are based upon the. Synthesis of novel quinazoline derivatives as antimicrobial agents article in chinese journal of chemistry 2. When the effervescence ceased, the precipitate obtained was filtered and washed with water. A onepot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following pdcatalyzed narylation, is also. 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. Dodecanoyl isothiocyanate i reacts additively with anthranilic acid to afford derivatives of thiourea ii and benzothiazine iiiin a onepot reaction. Quinazolinone has been considered as a magic moiety possessing myriad spectrum of medicinal activities. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. The biological activities of the synthesized quinazoline derivatives also. 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. Synthesis and reactivity of some novel quinazoline derivatives.
Pdf green approaches towards synthesis of substituted. Ep 1667992 b1 quinazoline derivatives the lens free. More recently, we have previously reported the synthesis of a series of novel quinazoline nitrogen mustard derivatives, and their potential antitumor activities. Jan 24, 2007 the invention concerns quinazoline derivatives of formula i.
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