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 method was a convenient and practical strategy for synthesis of 2substituted quinazoline derivatives that have only one phenyl substituent on heterocyclic. Synthesis and antimicrobial activity of some annelated quinazoline. Synthesis and cytotoxic evaluation of novel quinazolinone. Antibacterial bioassays indicated that most of target compounds exhibited significant antibacterial activities against xac and rs in vitro. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. 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. Catalystfree synthesis of quinazoline derivatives using low. A series of sulphonyl acetamide analogues were generated on the quinazoline ring through a multistep reaction starting from 2mercapto3hquinazolin4one. Most compounds showed good to excellent anticancer activity. Chinazolin was first proposed for this compound by weddige3, on observing that this was isomeric. The syntheses of 17 substances from this group among them 6 new ones have been complete.
Synthesis of novel quinazoline derivatives as antimicrobial agents. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. Synthesis of quinazoline derivatives ethanol initiated. Synthesis of some quinazoline derivatives was carried out with their plant protection capabilities in mind. Synthesis of some novel quinazoline derivatives having anticancer activity. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. Synthesis, characterization and evaluation of antifungal and. Quinazoline derivatives and heterocyclic annelated quinazolines are reported to be physiologically and pharmacologically active 1, which exhibit a wide rang of.
Design, synthesis and biological evaluation of novel quinazoline derivatives as potential anticancer agents ahmed m. 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 method for the pdcatalyzed narylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. A rhiicatalyzed transannulation of nsulfonyl1,2,3triazoles with 2,1benzisoxazoles provides quinazoline derivatives. 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 some novel quinazoline derivatives having. The biological activities of the synthesized quinazoline derivatives also are discussed.
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. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Pdf synthesis, cytotoxic evaluation and molecular docking. Design, synthesis and biological evaluation of spiro. Synthesis and antimicrobial activity of some new quinazoline. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. The invention concerns quinazoline derivatives of formula i. Synthesis and threedimensional quantitative structure.
Pharmaceutical college, guangxi medical university, nanning, guangxi, china. 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. The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. Design and synthesis of sulphonyl acetamide analogues of. Design, synthesis, and biological evaluation of quinazoline.
Abstract quinazoline isothiocyanate 1 reacts with various nucleophiles nitrogen nucleophiles, oxygen nucleophiles and sulphur nucleophiles to afford heterocyclic systemes 2. 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. Jun 03, 20 owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Chlorophenylamino 6methoxy quinazoline derivatives p. Synthesis and evaluation of new 2, 3and 2, 4disubstituted. 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. Pdf uses of 2ethoxy43h quinazolinone in synthesis of. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Uses of 2ethoxy43h quinazolinone in synthesis of quinazoline and quinazolinone derivatives of antimicrobial activity.
Synthesis of some novel quinazoline derivatives having anti. Catalystfree synthesis of quinazoline derivatives using. A onepot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following pdcatalyzed narylation, is also. Jun 25, 2015 synthesis, characterization and apoptotic activity of quinazolinone schiff base derivatives toward mcf7 cells via intrinsic and extrinsic apoptosis pathways. Highly efficient coppercatalyzed cascade 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. Synthesis and biological evaluation of 3,5diaryl isoxazolineisoxazole linked 2,3dihydroquinazolinone hybrids as anticancer agents. Design, synthesis and biological evaluation of novel. 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. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. An insight into the therapeutic potential of quinazoline derivatives as anticancer agents. Anthranilic acid was condensed with chloro acylchloride followed by.
The syntheses of 17 substances from this group among them 6 new ones have been completed. Synthesis and thermal decomposition kinetics of some. Undeniable pharmacological potentials of quinazoline motifs in. Journal of global trends in pharmaceutical sciences. Design, synthesis, and biological evaluation of novel quinazoline. Synthesis and evaluation of some new 4, 6 disubstituted. 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. Synthesis and antimicrobial activity of some new quinazoline derivatives dhaval j. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. Synthesis and anticancer activity of new quinazoline derivatives. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities.
Methoxyl, methyl, halogen, and trifluoromethyl groups on stilbeneamino were detected. Review on synthesis of bioactive pyrazoline derivatives. Efficient methods for synthesis of quinazolin4ones are e. Synthesis, spectral characterization, and antimicrobial. 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. From anthranilic acid and urea the fusion of anthranilic acid with urea gave 1,2,3,4tetrahydro2,4dioxoquinazoline see scheme 14. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives. The observed dipole moment of quinazoline in benzene is 2.
Quinazoline derivatives, which belong to the ncontaining heterocyclic compounds, have caused universal concerns due to their widely and. Synthesis and biological evaluation of quinazoline4thiones. Mar 25, 2020 a series of sulphonyl acetamide analogues were generated on the quinazoline ring through a multistep reaction starting from 2mercapto3hquinazolin4one. The newly synthesized derivatives have been characterized through. All the compounds were tested for antimicrobial activity. 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. The synthetic studies of the quinazoline derivatives discussed in this section are based upon the.
Pdf on dec, 2019, satyendra mishra and others published quinazolinone and quinazoline derivatives. The structures of the newly synthesized compounds were established by ir, 1 h nmr, c nmr, and mass spectral data. Potential of quinazoline and quinazolinone derivatives. Synthesis and thermal decomposition kinetics of some pyrazolo. Synthesis of novel quinazoline derivatives as antimicrobial agents article in chinese journal of chemistry 2. Ep 1667992 b1 quinazoline derivatives the lens free. Synthesis and biological evaluation of quinazoline. Structure of zd6474 and 2,4disubstituted quinazoline derivatives. According to the main method the authors adopted in their research design, those synthetic methods were divided. Synthesis, characterization and apoptotic activity of quinazolinone schiff base derivatives toward mcf7 cells via intrinsic and extrinsic apoptosis pathways. Anticancer evaluation, quinazoline derivatives, synthesis. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. Synthesis of some new quinazolinone derivatives and.
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. Synthesis and anticancer activity of new quinazoline. A more satisfactory synthesis of quinazoline was subsequently devised by gabriel in 1903 that studied properties and those of its derivatives in greater detail. Ashour2 1department of pharmaceutical chemistry, college of pharmacy, alkharj university, saudi arabia and 2department of. Palladiumcatalyzed nmonoarylation of amidines and a one. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. 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. When the effervescence ceased, the precipitate obtained was filtered and washed with water. 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. 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. 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. Design, synthesis, and biological evaluation of quinazoline derivatives as dual hdac1 and hdac6 inhibitors for the treatment of cancer. Quinazoline in 1905 riedel obtained a patent describing a synthesis of quinazoline from onitrobenzaldehyde through reaction with formamide to the onitrobenzylidenediformamide.
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 and reactivity of some novel quinazoline derivatives. Synthesis, characterization and evaluation of antifungal. Reduction of this with zinc and dilute acetic acid gave quinozoline in. 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. Quinazoline derivatives are well known to have a diverse array of therapeutic activities. Synthesis, characterization, and anticancer activity of new. Shakhidoyatov chemistry of heterocyclic compounds volume 35, pages 821 824 1999cite this article. 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.
The molecular manipulation of promising lead compound is still a major line of approach for the discovery of new drugs. 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. Synthesis of quinazoline derivatives containing veratrole and benzo15crown5 moieties. Marvania et al3 synthesized a series of phenyl n mustardquinazoline derivatives and. Synthesis, characterization, and anticancer activity of.
It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. It is a light yellow crystalline solid that is soluble in water. Chemical characteristics, synthetic methods, and biological. A series of quinazoline derivatives containing a 1,3,4oxadiazole moiety were synthesized and evaluated for their antibacterial activities against xanthomonas axonopodis pv. Some of the synthesized compounds are tested for its antimicrobial activity. The aim of this study was to discover new quinazoline derivatives with preventive effect on lipo polysaccharideinduced acute lung injury via anti inflammatory. Design, synthesis, characterization and antimicrobial. A few examples of quinazoline ring synthesis by ring contraction have also been reported. Wide range of quinazolinone biological properties including. 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.
Reduction of this with zinc and dilute acetic acid gave quinozoline in good yield. Review article chemical characteristics, synthetic methods. Synthesis of quinazoline derivatives containing veratrole and. Synthesis and evaluation of 2,4disubstituted quinazoline. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts. An especially popular procedure is based on the reaction of. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Oxidation catalytic hydrogenation of quinazoline stopped. The deaminative coupling reaction of 2aminobenzamides with amines led to the efficient formation of quinazolinone products.
Synthesis, characterization and apoptotic activity of. 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. Unfortunately, classic chemical synthesis does not provide an opportunity for the formation of n. 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. 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. Kamal a, bharathi ev, reddy js, ramaiah mj, dastagiri d, reddy mk, et al. According to the main method the authors adopted in their. The synthesis of some quinazoline derivatives and their.
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. Palladiumcatalyzed nmonoarylation of amidines and a onepot. 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. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Synthesis of quinazoline and quinazolinone derivatives via.