The in situ formed ruthenium catalytic system rul was found to be highly selective for the dehydrogenative coupling reaction of 2aminophenyl ketones with amines to form quinazoline products. Seven new quinazoline derivatives are synthesized by three steps. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Quinazolinones benzopyrimidine derivatives, are compounds with wide spectrum of biological activities, including. Synthesis and evaluation of some new 4, 6 disubstituted quinazoline derivatives for antimicrobial and antifungal activities chavan b. Design, synthesis, and dnabinding of nalkylanilino. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. All quinazoline derivatives showed significant antibacterial activity against tested pathogens. Reactions of organolithium reagents with quinazoline. Quinazoline and their derivatives constitute an important class of heterocyclic compounds.
Five trisubstituted quinazolones and eight trisubstituted quinazoline4thiones have been tested for antibacterial effects by a microdilution method. Synthesis of 4h3,1benzoxazines, quinazolin2ones, and. Ep0520722b1 therapeutic preparations containing quinazoline. For instance, quinazoline derivatives with imidazole substituted at the 2position of side chain own potent antiinflammatory function. Synthesis of quinazoline derivatives and their biological. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Synthesis of some new quinazolinone derivatives and. It has been used for the treatment of high blood pressure as adrenergic blockers, anxiety, and panic disorder prazosin and has also been found useful for epidermal growth factor.
Ajarimb a school of chemistry, cardiff university, main building, park place, cardiff cf10 3at, uk b criminal evidence, ministry of interior, riyadh 11632, p. Furthermore, the 1h nmr spectra of compounds 10ai showed signals in the range of. Synthesis of some novel quinazoline derivatives having. Novel quinazoline derivatives of sydnone 1463 observed at about. It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. Quinazoline is a bicyclic compound earlier known as benzo 1, 3diazine. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring.
Series of novel derivatives of quinazoline containing thiosemicarbazide moiety 5 and 9 have been synthesized and tested for their antitumor activities in vitro against a panel of five human cancer cell lines. Quinazoline nucleus is found in many bioactive natural products. The process is operationally simple and has a broad substrate scope. Facile synthesis of 3substituted quinazoline2,4dione. Synthesis and antioxidant properties of novel quinazoline. Unfortunately, classic chemical synthesis does not provide an opportunity for the formation of nphenyl quaternary 1,3diazinium compounds. The c nmr spectra exhibited confirmatory signals for the. 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. This method provides a synthetic methodology in obc. Quinazoline derivatives also known to show antibacterial activity2026. Synthesis of quinazoline derivatives containing veratrole.
Review article chemical characteristics, synthetic methods. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. The first example of a coppercatalyzed cascade reaction of 2aminophenylmethanols with aldehydes using the combination of cerium nitrate hexahydrate and ammonium chloride has been developed, leading to a wide range of 2substituted quinazolines in moderate to excellent yields. Thus, fusion of compound 3 with anthranilic acid in an oil bath at 165175 c afforded 4methyln48oxo8hquin azolino4,3bquinazolin6ylphenylbenzenesulfonamide 12. Quinazoline isothiocyanate 1 reacts with various nucleophiles nitrogen nucleophiles, oxygen nucleophiles and sulphur nucleophiles to afford heterocyclic systemes 2. Ho wev er, none of the synthesiz ed compounds w ere super ior to the standar d ofloxacin table2. Synthesis and antitumor activity of novel quinazoline. The detailed synthesis and their antimicrobial screening are reported. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. Synthesis, characterization, and anticancer activity of new. Chinazolin was proposed for its compound by weddige, on observing that this was isomeric with the then compound cinnoline and quinaoxaline. Isatoic anhydride, acid hydrazides or ammonium acetate and aromatic aldehydes in the presence of nhalosulfonamides. Oct 10, 20 a series of novel 1methyl3substituted quinazoline 2,4dione derivatives was designed, synthesized, and evaluated for their antimicrobial activities against six strains of bacteria and five fungi in vitro. The cascade reaction includes a sequential ullmanntype coupling and aerobic oxidation and provides a convenient and practical strategy for the synthesis of.
Synthesis, 3d pharmacophore, qsar and docking studies of novel quinazoline derivatives with nitric oxide release moiety as preferential cox2 inhibitors doaa boshra farag, a nahla a. On the basis of literature by chinese scientists on the effective antioxidant activity of schiff bases containing 2oxoquinoline and due to structural similarity of quinoline and quinazoline ring systems, the reactions of 3aminoquinazolinone with a range of aromatic aldehydes and ethoxymethylene derivatives have been carried out and their. Synthesis, anticancer and antimicrobial characterization of. The numbering of the quinazoline ring system which is currently used was suggested by paal and busch. Potential of quinazoline and quinazolinone derivatives. All synthesized compounds are confirmed by uv, ir, mass and h1nmr. Synthesis, anticancer and antimicrobial characterization. Several biological activities were reported for fused tricyclic quinazoline derivatives 8, 9 among which deoxyvasicinone is highly interesting and has been. Researchers have already determined many therapeutic activities of quinazoline derivatives, including anticancer, 1234 antiinflammation, 5,6, antibacterial, 789 10 analgesia. Synthesis of quinazoline and quinazolinone derivatives via. Aly synthesis and antimicrobial activity of some annelated quinazoline derivatives scheme 2. Quinazoline derivatives, which belong to the ncontaining heterocyclic compounds, have caused universal concerns due to their widely and. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. Synthesis, characterization, and anticancer activity of.
Synthesis of novel quinazoline4one derivatives and their. In this study, a new series of quinazoline derivatives 326 was synthesized and characterized via physicochemical and spectral means. Alkylation and hydrazinolysis of the inherent thioxo group in afforded the corresponding thioethers 423 and hydrazine derivatives. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. In this research, a facile, effective and onepot synthesis of new quinazoline41hone derivatives is reported. The bioactive assays showed that most of the compounds exhibited moderate antimicrobial activities against the tested strains. Pdf on dec, 2019, satyendra mishra and others published quinazolinone and quinazoline derivatives. Facile synthesis of 3substituted quinazoline2,4dione and 2.
Treatment of 2amino5methylbenzoic acid with butyl isothiocyanate resulted in the new 2thioxoquinazolin4one 3. Ebscohost serves thousands of libraries with premium essays, articles and other content including synthesis of novel quinazoline4one derivatives and their acyclonucleoside analogs. New 3amino quinazoline 4 one derivatives were prepared following the reaction sequences depicted inschemes 1. Synthesis of some novel quinazoline derivatives having anti. Synthesis of quinazoline derivatives containing veratrole and benzo15crown5 moieties. An effective and straightforward approach to the synthesis of 4h3,1benzoxazines 3 and 4, quinazolin2ones 5, and quinoline4one derivatives 6 and 7 is provided by palladiumcatalyzed cyclization. Quinazoline derivatives have been very well known for antihypertensive activity.
A simple and efficient, ligandfree coppercatalyzed approach to quinazoline derivatives uses readily available substituted 2bromophenylmethylamines and amides as starting materials. Synthesis and reactivity of some novel quinazoline derivatives. The reaction enables great flexibility of the substitution patterns on quinazolines and is applicable to two different nitriles to give a regioselective product. Synthesis of quinazoline derivatives containing veratrole and. Synthesis and antimicrobial activity of some annelated. The structure of synthesized compounds was confirmed by the results from elemental analyses table 1 and 1h nmr spectra table 2 in which signals for the protons of all the. Oxidation catalytic hydrogenation of quinazoline stopped after the absorption of one molecules of hydrogen and. A onepot protocol has been developed for the synthesis of quinazolinones from amideoxazolines with tscl via a cyclic 1,3azaoxonium intermediate and 6. 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. New n alkylanilinoquinazoline derivatives 5, 12, 20, and 22 have been prepared from 4chloro6,7dimethoxyquinazoline 3, 4chloro6,7methylenedioxyquinazoline 19, and commercially available anilines.
An efficient onepot approach to multiple substituted quinazolines with diaryliodonium salt 1, and two nitriles 2 has been presented. Quinazoline is an organic compound with the formula c 8 h 6 n 2. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives. The synthesized compounds were characterized by spectral methods. 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.
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. Chemical characteristics, synthetic methods, and biological. Synyhesis and antibacterial activities of new 3amino2. 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. In view of the above, the design and synthesis of newer antibacterials is an area of. Compounds brq, no 2q and c1q were not active against staphylococus. All the compounds were active against klebsiella aerugenes and salmonella typhi. A series of novel 1methyl3substituted quinazoline2,4dione derivatives was designed, synthesized, and evaluated for their antimicrobial activities against six strains of bacteria and five fungi in vitro. Synthesis, characterisation and biological evaluation of.
Synthesis and anticancer activity of new quinazoline derivatives. The catalytic coupling method provides an efficient synthesis of. Molinspiration software was used to analyze lipinski rule of five and drug likeness properties. Quinazoline derivatives are well known to have a diverse array of therapeutic activities. Oct 17, 2012 3substituted quinazoline2,41h,3hdione and 2,3disubstituted quinazolineone derivatives attract considerable interest due to their pharmacological properties. 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. Many of them show insecticidal, analgesic, antifungal, antibacterial, anticancer, antiinflammatory activities. The observed dipole moment of quinazoline in benzene is 2. 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 antihypertensive activity of some quinazoline.
Antibacterial effects of trisubstituted quinazoline. 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. Because of these reasons much attention is being paid for the synthesis of. Certain quinazoline derivatives showed a remarkable activity against the opportunistic.
Synthesis, characterization and evaluation of antifungal. The deaminative coupling reaction of 2aminobenzamides with amines led to the efficient formation of quinazolinone products. Insilico design of novel analogues were carried out using acd labs chem sketch 12. Synthesis and anticancer activity of new quinazoline. Quinazoline derivatives are one of the most important sixmembered nitrogencontaining heterocyclic compounds as many naturally occurring and pharmaceutical compounds contain quinazoline moiety as the core unit. Synthesis of novel quinazoline derivatives as antimicrobial. Introduction in recent years there has been considerable interest in the synthesis of substituted quinazoline derivatives due to their pharmacological activities1. Catalystfree synthesis of quinazoline derivatives using. Catalystfree synthesis of quinazoline derivatives using low. In the first part of this study 2methyl43hbenzoxazin4one was obtained from the reaction of anthranilic acid with acetic anhydride, the reaction proceeds by the attack of.
All synthesized compounds are confirmed by uv, ir, mass and. Synthesis, 3d pharmacophore, qsar and docking studies of. A simple and efficient approach for the synthesis of 2aminoquinazoline derivatives in moderate to good yields. The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. The quinazoline skeleton appears in many alkaloids, most commonly in the form of 43hquinazolinone moieties. Quinazoline derivatives, whi ch belong to the ncontaining heterocyclic compounds, have caused universal concerns due to their widely and distinct biopharmaceutical activities. Synthesis leading to novel 2,4,6trisubstituted quinazoline. Unexpected coppercatalyzed cascade synthesis of quinazoline. Reactions of organolithium reagents with quinazoline derivatives. Synthesis of the derivatives of quinazoline 4 and 5. On n quinoxaline the synthetic studies of the quinazoline derivatives discussed in this section are based upon the following substitution patterns of the ring system. Jun 03, 20 for instance, quinazoline derivatives with imidazole substituted at the 2position of side chain own potent antiinflammatory function. Shakhidoyatov chemistry of heterocyclic compounds volume 35, pages 821 824 1999cite this article. I 43hquinazolinones 1 and related quinazolines 2 are classes.
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