A new and facile preparation of quinazoline 2,41h,3hdiones was first reported which was the condensation of aromatic oaminonitriles with dmf or n,ndiethylformamide in the presence of zncl2 0. Facile synthesis of 3substituted quinazoline2,4dione and 2. Shakhidoyatov chemistry of heterocyclic compounds volume 35, pages 821 824 1999cite this article. Different substituents have been introduced, first in position 4, then in position 2 and 4 of quinazoline, then two substituents to both rings e. Some of the known quinazoline derivative are reported to exhibit remarkable anticancer activity11. Quinazoline is a bicyclic compound earlier known as benzo 1, 3diazine.
Reactions of organolithium reagents with quinazoline. Synthesis, characterization, and anticancer activity of new. All synthesized compounds are confirmed by uv, ir, mass and h1nmr. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.
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. Numerous quinazoline derivatives have been found to possess a broad spectrum of biological activities, which. The selectivity of 2csp csp2 bond formation in this case is attributed to the increased reactivity of the c4 position of the quinazoline ring due to the. Synthesis, characterization and antimicrobial studies of. General procedure for synthesis of quinazoline schiff. Oxidation catalytic hydrogenation of quinazoline stopped.
Green synthesis of substituted anilines and quinazolines from. Chinazolin was proposed for its compound by weddige, on observing that this was isomeric with the then compound cinnoline and quinaoxaline. Quinazoline nucleus has attracted attention of medicinal chemists, due to wide spectr um of biological activities exhibited by them. The corresponding quinazoline8cyano derivatives 21 can be synthesized by treating in situgenerated nitriletea salt with amines and coupling. Synthesis of quinazoline derivatives containing veratrole and. Quinazoline derivatives have a therapeutic benefit as an anti invasive agents with potential activity in early and advanced solid tumors, metastatic bone disease and leukemias610. Aly synthesis and antimicrobial activity of some annelated quinazoline derivatives scheme 2.
Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. A series of novel thiazolo quinazoline derivatives by condensation of different aromatic aldehydes with 4nitro aniline are screened for antioxidant activity by dpph radical assay, nitric oxide scavenging activity, and hydrogen peroxide scavenging activity and reported that synthesized compounds 9799 were found to be the most potent. Reactions of organolithium reagents with quinazoline derivatives gamal a. Pdf synthesis of some new quinazolinone derivatives and.
The cascade reaction includes a sequential ullmanntype coupling and aerobic oxidation and provides a convenient and practical strategy for the synthesis of. Quinazoline has become a popular topic up of two fused sixmembered simple aromatic rings, a benzene ring and a pyrimidine ring having due to its manifold uses. Synthesis and reactivity of some novel quinazoline derivatives. Coppercatalyzed sequential narylation and aerobic oxidation. Ep0520722b1 ep19920305703 ep92305703a ep0520722b1 ep 0520722 b1 ep0520722 b1 ep 0520722b1 ep 19920305703 ep19920305703 ep 19920305703 ep 92305703 a ep92305703 a ep 92305703a ep 0520722 b1 ep0520722 b1 ep 0520722b1 authority ep european patent office prior art keywords chloro quinazoline 4c pharmaceutically formula prior art date 19910628 legal status the. 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. Synthesis and characterization of novel quinazoline derivatives via reaction of isatoic anhydride with schiffs base. Recent structures with potent anticancer activity february 2018 in book. Synthesis of quinoline derivatives by a doebnervon miller. Based on the importance of quinazoline moiety for its anticancer activity, and referring to the structure characteristics of gefitinib, erlotinib and lapatinib, we chose 4arylamino6furan2ylquinazoline as a core structure, 3 classes of new quinazoline derivatives 11 compounds were. Synthesis of novel hybrids of quinazoline and artemisinin.
Facile synthesis of 3substituted quinazoline2,4dione. Jun 03, 20 for instance, quinazoline derivatives with imidazole substituted at the 2position of side chain own potent antiinflammatory function. Oxidation catalytic hydrogenation of quinazoline stopped after the absorption of one molecules of hydrogen and. Pdf synthesis, characterization, and anticancer activity of new. An efficient synthesis of quinazoline and xanthene. In addition several quinazoline derivatives posses diverse. Recently, many efforts have been focused by chemists on the modification of quinazoline ring for development of pharmaceutical and clinical compounds. The 2aminobenzylamine derivatives and quinazoline products were. Design, synthesis, and dnabinding of nalkylanilino. Quinazoline and condensed quinazolines ha ve exhibited a v ariety of biolo gical acti vities lik e analg esic, antiinf lammator y1, antihypertensive2, antihistaminic, anticancer35, sedative, hypnotic and. These metrics are regularly updated to reflect usage leading up to the last few days.
Basepromoted synthesis of 2aryl quinazolines from 2. Five trisubstituted quinazolones and eight trisubstituted quinazoline4thiones have been tested for antibacterial effects by a microdilution method. Synthesis of quinazoline derivatives containing veratrole. 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. Seven new quinazoline derivatives are synthesized by three steps. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. Thus, fusion of compound 3 with anthranilic acid in an oil bath at. Synthesis and thermal decomposition kinetics of some. Synthesis and anticancer activity of new quinazoline derivatives.
Design, synthesis, and dnabinding of n alkylanilinoquinazoline derivatives. Synthesis and antihypertensive activity of some quinazoline. Quinazoline is an organic compound with the formula c 8 h 6 n 2. 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. It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. Synthesis and bioactivities article pdf available in chemistry central journal 71.
Review article chemical characteristics, synthetic methods. Synthesis of quinazoline derivatives and their biological. Based on the importance of quinazoline moiety for its anticancer activity, and referring to the structure characteristics of gefitinib, erlotinib and lapatinib, we chose 4arylamino6furan2yl quinazoline as a core structure, 3 classes of new quinazoline derivatives 11 compounds were. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. A novel and efficient coppercatalyzed cascade method for the synthesis of quinazolines in good yields uses readily available substituted 2bromophenylmethylamines and amidine hydrochlorides as the starting materials, inexpensive cubr as the catalyst, and economical and environment friendly air as the oxidant. Numerous quinazoline derivatives have been found to possess a broad spectrum of biological activities, which stimulated the research activity in this field. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Synthesis, characterization, and anticancer activity of new quinazoline derivatives against mcf7 cells. A rhiicatalyzed transannulation of nsulfonyl1,2,3triazoles with 2,1benzisoxazoles provides quinazoline derivatives. Wide range of quinazolinone biological properties including. In this context, ligandbased virtual screening studies allowed us to identify thiadiazine and quinazoline derivatives as a new class of pde7 inhibitors. Ep0520722b1 therapeutic preparations containing quinazoline. To develop a lead antidiabetic compound, a series of 21 novel quinazoline derivatives have been synthesized and screened against. Herein, we report the design, synthesis, and biological evaluation of some novel quinazoline derivatives.
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. Several biological activities were reported for fused tricyclic quinazoline derivatives 8, 9 among which deoxyvasicinone is highly interesting and has been. Ajarimb a school of chemistry, cardiff university, main building, park place, cardiff cf10 3at, uk. The emerging understanding of quinazoline derivatives on their pharmacological target. New n alkylanilinoquinazoline derivatives 5, 12, 20, and 22 have been prepared from 4chloro6,7dimethoxyquinazoline 3, 4chloro6,7methylenedioxyquinazoline 19, and commercially available anilines. Design, synthesis, and biological evaluation of quinazoline. The binding model suggests one to four hydrogen bonding interactions between quinazoline derivatives and. Synthesis of quinazoline derivatives containing veratrole and benzo15crown5 moieties. Insilico design of novel analogues were carried out using acd labs chem sketch 12. It is a light yellow crystalline solid that is soluble in water. Facile access to potent antiviral quinazoline heterocycles with. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6.
Synthesis and anticancer activity of new quinazoline. Synthesis, structural analysis, and biological evaluation of. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Synthesis and in vitro biological evaluation of novel. These scaffolds further modified at c4 position using amidation method to generate 21 compounds. 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. Antibacterial effects of trisubstituted quinazoline derivatives. Quinazolinones benzopyrimidine derivatives, are compounds with wide spectrum of biological activities, including. 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. Anthranilic acid was condensed with chloro acylchloride followed by. Synthesis and antimicrobial activity of some annelated. Alkylation and hydrazinolysis of the inherent thioxo group in afforded the corresponding thioethers 423 and hydrazine derivatives.
Antibacterial effects of trisubstituted quinazoline. Many quinazoline derivatives have been synthesized over the last few decades. Advances in metalcatalyzed crosscoupling reactions of. The synthesis of some quinazoline derivatives and their. Pdf two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for. Synthesis and antihypertensive activity of some quinazoline derivatives harsha u. Synthesis, characterization and evaluation of antifungal and. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. Synthesis and thermal decomposition kinetics of some pyrazolo. Synthesis of carbazoles by a merged visible light photoredox and palladiumcatalyzed process. Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. Quinazoline derivatives have been very well known for antihypertensive activity.
Molinspiration software was used to analyze lipinski rule of five and drug likeness properties. Ajarimb a school of chemistry, cardiff university, main building, park place, cardiff cf10 3at, uk b criminal evidence, ministry of interior, riyadh 11632, p. The binding mode of the compounds at the active site of. Synthesis and antimicrobial activity of some new quinazoline. 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. The 2 aminobenzylamine derivatives and quinazoline products were. Synthesis of novel hybrids of quinazoline and artemisinin with high. 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. Chemical characteristics, synthetic methods, and biological.
The numbering of the quinazoline ring system which is currently used was suggested by paal and busch. The syntheses of 17 substances from this group among them 6 new ones have been completed. Synthesis of some quinazoline derivatives was carried out with their plant protection capabilities in mind. Synthesis of quinoline derivatives by a doebnervon miller reaction using a ag i exchanged montmorillonite k10 catalyst dissertation submitted to the university of kwazulunatal for the degree of master of science in chemistry by janeeka jayram school of chemistry and physics university of kwazulunatal january 2016. Oct 17, 2012 3substituted quinazoline2,41h,3hdione and 2,3disubstituted quinazolineone derivatives attract considerable interest due to their pharmacological properties. Synthesis, characterization, and anticancer activity of.
A brief survey about biological importance of quinazoline and thier derivatives revealed that a large number of publications began to appear after 1960s. Synthesis and antimicrobial activity of some new quinazoline derivatives dhaval j. Reactions of organolithium reagents with quinazoline derivatives. Synthesis of some novel quinazoline derivatives having anticancer activity. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. Synthesis, characterization and apoptotic activity of. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. 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. Five trisubstituted quinazolones and eight trisubstituted quinazoline 4thiones have been tested for antibacterial effects by a microdilution method.
Synthesis, characterization and evaluation of antifungal. Synthesis and antimicrobial evaluation of some new. Synthesis of some new quinazolinone derivatives and. A simple and efficient, ligandfree coppercatalyzed approach to quinazoline derivatives uses readily available substituted 2bromophenylmethylamines and amides as starting materials. Synthesis of some novel quinazoline derivatives having. Citations are the number of other articles citing this article, calculated by crossref and updated daily.35 850 984 1324 1069 225 417 1071 785 1197 312 212 447 178 268 596 989 817 470 848 1004 260 1420 1490 1476 905 9 347 29 975 1205 851 125 928 1476 641 265 63