Palladiumcatalyzed nmonoarylation of amidines and a onepot. Design, synthesis and biological evaluation of novel quinazoline derivatives as potential anticancer agents ahmed m. Jun 25, 2015 synthesis, characterization and apoptotic activity of quinazolinone schiff base derivatives toward mcf7 cells via intrinsic and extrinsic apoptosis pathways. The deaminative coupling reaction of 2aminobenzamides with amines led to the efficient formation of quinazolinone products. Synthesis, characterization and apoptotic activity of quinazolinone schiff base derivatives toward mcf7 cells via intrinsic and extrinsic apoptosis pathways. In this paper, condensation of 2aminobenzamide 1 with benzoyl chlorides 2 in the presence of sbaprso3h as a heterogeneous and reusable nano catalyst for the synthesis of benzamide derivatives 3 and some quinazolinone derivatives 4 was studied scheme 1. Synthesis and biological evaluation of 3,5diaryl isoxazolineisoxazole linked 2,3dihydroquinazolinone hybrids as anticancer agents. Synthesis and anticancer activity of new quinazoline derivatives. Synthesis and evaluation of 2,4disubstituted quinazoline. Synthesis of quinazoline derivatives ethanol initiated.
With this rationale, the synthesis and biological evaluation of new 4, 6disubstituted quinazoline derivatives was undertaken through various synthetic routes. Quinazoline is the main fused heterocyclic ring system reported for their biological activities, compounds with varieties of pharmacophores, which bring together knowledge of a target with understanding of the molecule types that might interact with the target family. Design and synthesis of sulphonyl acetamide analogues of. Review on synthesis of bioactive pyrazoline derivatives.
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. Pharmaceutical college, guangxi medical university, nanning, guangxi, china. Chlorophenylamino 6methoxy quinazoline derivatives p. Synthesis and thermal decomposition kinetics of some. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts. The synthesis of some quinazoline derivatives and their.
Review article chemical characteristics, synthetic methods. Abstract quinazoline isothiocyanate 1 reacts with various nucleophiles nitrogen nucleophiles, oxygen nucleophiles and sulphur nucleophiles to afford heterocyclic systemes 2. Design, synthesis and biological evaluation of spiro. Catalystfree synthesis of quinazoline derivatives using. Synthesis and cytotoxic evaluation of novel quinazolinone. Quinazoline in 1905 riedel obtained a patent describing a synthesis of quinazoline from onitrobenzaldehyde through reaction with formamide to the onitrobenzylidenediformamide. The invention concerns quinazoline derivatives of formula i. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives.
Kamal a, bharathi ev, reddy js, ramaiah mj, dastagiri d, reddy mk, et al. Synthesis of some novel quinazoline derivatives having anti. A rhiicatalyzed transannulation of nsulfonyl1,2,3triazoles with 2,1benzisoxazoles provides quinazoline derivatives. 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. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Synthesis of some new quinazolinone derivatives and. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. Synthesis and antimicrobial activity of some new quinazoline derivatives dhaval j. A series of quinazoline derivatives containing a 1,3,4oxadiazole moiety were synthesized and evaluated for their antibacterial activities against xanthomonas axonopodis pv.
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. The syntheses of 17 substances from this group among them 6 new ones have been completed. Shakhidoyatov chemistry of heterocyclic compounds volume 35, pages 821 824 1999cite this article. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Structure of zd6474 and 2,4disubstituted quinazoline derivatives. Synthesis, characterisation and biological evaluation of. Most compounds showed good to excellent anticancer activity.
Synthesis and reactivity of some novel quinazoline derivatives. Synthesis of novel quinazoline derivatives as antimicrobial agents. Some of the synthesized compounds are tested for its antimicrobial activity. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means.
Unfortunately, classic chemical synthesis does not provide an opportunity for the formation of n. Methoxyl, methyl, halogen, and trifluoromethyl groups on stilbeneamino were detected. Synthesis of some quinazoline derivatives was carried out with their plant protection capabilities in mind. An especially popular procedure is based on the reaction of. 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. Marvania et al3 synthesized a series of phenyl n mustardquinazoline derivatives and. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Reduction of this with zinc and dilute acetic acid gave quinozoline in.
Synthesis and anticancer activity of new quinazoline. Quinazoline derivatives, which belong to the ncontaining heterocyclic compounds, have caused universal concerns due to their widely and. Synthesis, characterization, and anticancer activity of. The method was a convenient and practical strategy for synthesis of 2substituted quinazoline derivatives that have only one phenyl substituent on heterocyclic. Synthesis of novel quinazoline derivatives as antimicrobial agents article in chinese journal of chemistry 2. According to the main method the authors adopted in their. Catalystfree synthesis of quinazoline derivatives using low. 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. Ashour2 1department of pharmaceutical chemistry, college of pharmacy, alkharj university, saudi arabia and 2department of. Synthesis and antimicrobial activity of some annelated quinazoline. View enhanced pdf access article on wiley online library html view download pdf for offline viewing.
Highly efficient coppercatalyzed cascade synthesis of. 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. Synthesis and biological evaluation of quinazoline. 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.
Design, synthesis, and biological evaluation of quinazoline. Undeniable pharmacological potentials of quinazoline motifs in. The synthetic studies of the quinazoline derivatives discussed in this section are based upon the. Quinazoline derivatives and heterocyclic annelated quinazolines are reported to be physiologically and pharmacologically active 1, which exhibit a wide rang of. An insight into the therapeutic potential of quinazoline derivatives as anticancer agents.
Synthesis and evaluation of new 2, 3and 2, 4disubstituted. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. From anthranilic acid and urea the fusion of anthranilic acid with urea gave 1,2,3,4tetrahydro2,4dioxoquinazoline see scheme 14. Design, synthesis, and biological evaluation of novel quinazoline. Anticancer evaluation, quinazoline derivatives, synthesis. 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. 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 threedimensional quantitative structure. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research.
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. Efficient methods for synthesis of quinazolin4ones are e. Synthesis, characterization and evaluation of antifungal and. Design, synthesis, characterization and antimicrobial. According to the main method the authors adopted in their research design, those synthetic methods were divided. Pdf on dec, 2019, satyendra mishra and others published quinazolinone and quinazoline derivatives.
Synthesis of some novel quinazoline derivatives having anticancer activity. Mar 25, 2020 a series of sulphonyl acetamide analogues were generated on the quinazoline ring through a multistep reaction starting from 2mercapto3hquinazolin4one. The biological activities of the synthesized quinazoline derivatives also are discussed. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Synthesis and thermal decomposition kinetics of some pyrazoloquinazoline derivatives shipra baluja, paras ramavat, kajal nandha physical chemistry laboratory, department of chemistry, saurashtra university, rajkot 360005, gujarat, india email address. Novel series of spiro2h,3h quinazoline 2,1cyclohexane derivatives ixvi were synthesized and biologically evaluated as cytotoxic agents against human breast carcinoma cell lines mcf7 using doxorubicin as a reference drug. Jun 03, 20 owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. All the compounds were tested for antimicrobial activity.
Antibacterial bioassays indicated that most of target compounds exhibited significant antibacterial activities against xac and rs in vitro. Quinazoline derivatives are well known to have a diverse array of therapeutic activities. According to the structural features of zd6474, we synthesized a series of 2,4disubstituted quinazoline derivatives figure 1, hoping to screen for new and better inhibitors of angiogenesis. Design, synthesis and biological evaluation of novel. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. 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. Pdf synthesis, cytotoxic evaluation and molecular docking. A series of sulphonyl acetamide analogues were generated on the quinazoline ring through a multistep reaction starting from 2mercapto3hquinazolin4one. 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. Ep 1667992 b1 quinazoline derivatives the lens free. Ethanol initiated titanocene lewis acid catalyzed diversity oriented synthesis of quinazoline derivatives yanlong luo, ya wu, yunyunwang, huaming sun, zunyuan xie, weiqiang zhang and ziwei gao key laboratory of applied surface and colloid chemistry ministry of education, school of. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring.
Synthesis, characterization, and anticancer activity of new. A more satisfactory synthesis of quinazoline was subsequently devised by gabriel in 1903 that studied properties and those of its derivatives in greater detail. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. Palladiumcatalyzed nmonoarylation of amidines and a one. Synthesis of some novel quinazoline derivatives having. The molecular manipulation of promising lead compound is still a major line of approach for the discovery of new drugs. A onepot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following pdcatalyzed narylation, is also. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. Synthesis and thermal decomposition kinetics of some pyrazolo. Synthesis of quinazoline and quinazolinone derivatives via. Uses of 2ethoxy43h quinazolinone in synthesis of quinazoline and quinazolinone derivatives of antimicrobial activity. Design, synthesis, and biological evaluation of quinazoline derivatives as dual hdac1 and hdac6 inhibitors for the treatment of cancer.
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. 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. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. Synthesis and antimicrobial activity of some new quinazoline. 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 methyl 2halobenzoates, and the method is of simple, economical and practical advantages. It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. Potential of quinazoline and quinazolinone derivatives. Quinazoline 1 is a fused bicycle compound earlier known as benzo1 3diazine was first prepared in the laboratory by gabriel1 in 1903, although one of its derivatives was known much earlier2. Oxidation catalytic hydrogenation of quinazoline stopped. The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry.
The observed dipole moment of quinazoline in benzene is 2. Chemical characteristics, synthetic methods, and biological. 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. 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. Anthranilic acid was condensed with chloro acylchloride followed by.
Pdf uses of 2ethoxy43h quinazolinone in synthesis of. Synthesis and biological evaluation of quinazoline4thiones. Synthesis and evaluation of some new 4, 6 disubstituted. Journal of global trends in pharmaceutical sciences. A method for the pdcatalyzed narylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. Reduction of this with zinc and dilute acetic acid gave quinozoline in good yield. Synthesis, characterization and evaluation of antifungal. A few examples of quinazoline ring synthesis by ring contraction have also been reported. The newly synthesized derivatives have been characterized through. 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.
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. Synthesis of quinazoline derivatives containing veratrole and. Alkylation and hydrazinolysis of the inherent thioxo group in afforded the corresponding thioethers 423 and hydrazine derivatives. Chinazolin was first proposed for this compound by weddige3, on observing that this was isomeric. The aim of this study was to discover new quinazoline derivatives with preventive effect on lipo polysaccharideinduced acute lung injury via anti inflammatory. Synthesis, characterization and apoptotic activity of. The structures of the newly synthesized compounds were established by ir, 1 h nmr, c nmr, and mass spectral data. Synthesis, spectral characterization, and antimicrobial. The syntheses of 17 substances from this group among them 6 new ones have been complete. It is a light yellow crystalline solid that is soluble in water.
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