A facile electrochemical method for synthesis of new. Electrooxidation enables highly regioselective dearomative. Synthesis of new benzofuran2carboxylic acid derivatives. A series of novel hybrid compounds between benzofuran and naryl piperazine have been synthesized and screened in vitro for antiinflammatory activity in lipopolysaccharide lpsstimulated raw264. The possible reaction mechanism for the formation of intermediate substituted phenanthro9,10bbenzofuran and. Methods for the synthesis of benzofuran derivatives. Two novel phenanthro9,10bbenzofuran and pyreno4,5bbenzofuran modified twistacene derivatives 9 and 10 have been successfully synthesized via suzuki coupling and characterized.
Design, synthesis and evaluation of benzofuranacetamide. Synthesis and biological activities of some benzofuran. Natural source, bioactivity and synthesis of benzofuran derivatives. A series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were synthesized as potential antitumor agents. In addition, hydrolysis of one of the nsulfonyl derivatives offered the. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Benzofuran is maillard produced present in roasted coffee aroma. Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent ashok k. Mar 18, 2015 benzophospholo3,2bbenzofuran bpbf derivatives were studied as a new family of phospholecontaining. Cyclization conditions and reaction mechanism for t r a n s f o r m a t i o n of. Synthesis, characterization, and anticancer activity of. General procedure for the synthesis of n4oxothiazolidin3yl benzofuran 2carboxamide derivatives 6ag an equimolar mixture of schiff bases 4ae and thioacetic acid, and the catalytic amount of anhydrous zncl 2 was taken in dmf and refluxed for 68 h.
The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. Synthesis of benzofuran derivatives via rearrangement and. Synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. The synthesized compounds were tested against human liver carcinoma cell line hepg2 and. Institute of biology and molecular patologies ibpm, department of. Titaniumiii chloride mediated synthesis of furan derivatives 425 table 1. Benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc. Us5919955a combinatorial solid phase synthesis of a library. An efficient synthesis of benzofuran derivatives under. Furthermore, these continuous reactions could be achieved. Synthesis of anthra2,3ibenzofuran derivatives by cyclization of laccaic acid a derivatives and its reaction mechanism dingyu hu, yoshihiko shinoda, and shinichi nakatsuka t h e united graduate school of agricultural science, g i f u u n i v e r s i t y, yanagido, g i f u 5 0 1 1 1, japan a b s t r a c t. We report on a novel synthesis towards benzofuran 2ylmethanamine and indol2ylmethanamine derivatives by using orthomethoxy and orthonitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole4carboxylic acid methylester moiety was produced.
When this process was carried out in boiling methanol for 16 hours the target benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a and 3b were obtained in moderate yields. Simple and efficient synthesis of benzofuran derivatives from tyrosol paolo bovicelli1, fabrizio bottaro1, carla sappino1, michela tomei1, valentina nardi1, ilaria proietti silvestri1, beatrice macchi2, caterina frezza2, giuliana righi1 1c. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Design, synthesis, and biological evaluation of novel. Benzofuran is a constituent of coix lachrymajobi jobs tears and gentiana lutea yellow gentian benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Substituted benzofurans also posses other applications such as fluorescent sensor, antioxidants, oxidant, brightening agents and in other field of chemistry and agriculture. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents.
Physical properties of 3 benzofuran 2yl1phenyl pyrazoline derivatives 610. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. Harmalkar, xuezhen xu, kyusic jang, kyeong lee bk21plus rfind team, college of pharmacy, dongguk universityseoul, goyang 410820, republic of korea a r t i c l e i n f o a b s t r a c t. Davood nematollahi, davood habibi, mohammad rahmati, mohammad rafiee. Titanoceneiii chloride mediated synthesis of furan derivatives. Synthesis and biological evaluation of new benzofuran carboxamide. This methodology is appreciated in terms of chemoselectivity and mild reaction conditions. Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial. Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. Synthesis, antimicrobial, and antioxidant activity of. The benzofuran substituted chalcones showed anticancer activity on pc3 and mcf7 cell lines.
These synthesized compounds were screened for in vivo anticancer activity. Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Synthesis of benzofuran derivatives through cascade radical. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives 23, 27, and 28, respectively. Synthesis and biological evaluation of new benzofuran. Pdf natural source, bioactivity and synthesis of benzofuran. In addition to the above, benzofuran derivatives possess a wide range of biological activities such as antimicrobial, antitumor, antiinflammatory 68. Numerous synthesized benzofuran derivatives were found to be biologically active 7, 8, 9. Volume 21, issue 12, december 2010, pages 14391442.
The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. It is the parent of many related compounds with more complex structures. Benzofuran is the parent of many related compounds with more complex structures. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives. Derivatives from tyrosol simple and efficient synthesis of. It may also be formed during other uses of coal or oil. Novel benzofuran derivatives bearing naryl piperazine moiety. Therefore, the novel singlestep synthesis of compounds 3af, 5ae using a solid catalyst was performed.
The structures of all compounds were established on the basis of analytical and spectral data. The present study deals with the synthesis of some substituted pyrazolines with. All of the benzofuran derivatives have weak antiache activities compared with. A novel series of chalcones, 3aryl15bromo1 benzofuran. Pdf a series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to. These compounds are important intermediates for the synthesis of a variety of. Novel synthesis of benzofuran and indol2ylmethanamine. It is essentially prepared via alkaline hydrolysis of khellin, a natural furanochromone isolated from ammi visnaga l. During a synthesis of coumarins to obtain new candidates for treating alzheimers disease ad, an unusual rearrangement of a benzopyran group to a benzofuran group occurred, offering a novel synthesis pathway of these benzofuran derivatives. Expanded benzofurandecorated twistacene derivatives. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin. Pdf 2acetyl benzofuran 1 was synthesized by refluxing. The structure of this compound was determined as benzofuran derivative. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties.
Synthesis of 2,3difunctionalized benzofuran derivatives through. We report on a novel synthesis towards benzofuran2ylmethanamine and indol2ylmethanamine derivatives by using orthomethoxy and orthonitro substituted phenylacetic acids as starting material, respectively. Synthesis, anticancer and molecular docking studies of. Natural source, bioactivity and synthesis of benzofuran derivatives article pdf available in rsc advances 947. Benzofuran synthesis through iodocyclization reactions.
The synthesis and spectral properties of benzofuran. In addition, several reports have pointed out the value of some synthetic benzofuran derivatives, containing a heterocyclic substituent linked at c2 of benzofuran nucleus, as antitumor agents. Synthesis of benzofuran derivatives through cascade. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. Synthesis and characterization of some new pyrazoline. A green method for synthesis of new benzofuran derivatives. Journal of chemical and pharmaceutical research, 2017, 95. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Sep 21, 2016 benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc.
Synthesis and properties of benzophospholo3,2bbenzofuran. Compounds 5s, 5r and 17b displayed the highest anticancer activity against ehrlich ascites. The successful use of various iodinating agents, bases, additives etc. It is well known that vitamin e having chroman skeleton have a. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. Two novel phenanthro9,10b benzofuran and pyreno4,5b benzofuran modified twistacene derivatives 9 and 10 have been successfully synthesized via suzuki coupling and characterized. Dubois, synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth, bioorg.
Issn 22293566 synthesis and biological activity of furan derivatives verma anupam, pandeya s. Many methodologies for the synthesis of benzofuran2carboxylic acid skeleton were developed and most of them are based on the reaction of salicylaldehydes with haloacetates followed by cyclization of formylphenoxyacetic acid derivatives intermediates 1117. The excess dmf was distilled off and the reaction mixture was poured into ice. Entry enol ether 2 reactant alcohol used furan derivative 4 yield %a 1 63 2 68 3 64 4 54 5 53 6 51 7 52b 8 58 ayield refer to pure isolated product 4 from 2. Synthesis of anthra2,3i benzofuran derivatives by cyclization of laccaic acid a derivatives and its reaction mechanism dingyu hu, yoshihiko shinoda, and shinichi nakatsuka t h e united graduate school of agricultural science, g i f u u n i v e r s i t y, yanagido, g i f u 5 0 1 1 1, japan a b s t r a c t. Synthesis, characterization, and anticancer activity of new. Benzophospholo3,2bbenzofuran bpbf derivatives were studied as a new family of phospholecontaining. This colourless solid is a component of the coal tar. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring. For example, compound a 11, compound b 12 and compound c have been synthesized and evaluated as potent antitumor agents figure 1.
Due to the presence of benzofuran moiety, they have a. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. Structure activity relationships between these chalcone derivatives and starting material d1 demonstrated that benzofuran substituted chalcones showed more potent activities than. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Pdf synthesis of benzofuran derivatives and their evaluation of. All the newly synthesized compounds were confirmed by spectral studies. General procedure for synthesis of benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran2carboxylic acid ethyl esters 2a or 2b 0. Design, synthesis and evaluation of benzofuran acetamide scaffold as potential anticonvulsant agent ashok k. The three patterns of reactivity observed for the o.
A facile electrochemical method for synthesis of new benzofuran derivatives. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. Synthesis of benzofuran derivatives via different methods. Exploitation of donoracceptor cyclopropanes and nsulfonyl 1. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. The synthesis and antimicrobial activity of some novel 11benzofuran2yl2 mesitylethanone derivatives eur. Breaking the aromatic systems of electronrich arenes or heteroarenes provides threedimensional chemicals of high added value 1,2,3,4,5,6,7.
A series of novel benzofuran scaffolds of amino pyrimidines 5a5s and azetidinones 17a17j were synthesized as potent biheterocyclic molecules. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. For example, psoralen is a benzofuran derivative that occurs in several plants. Development of dualacting benzofurans for thromboxane a2. The benzofuran derivatives are naturally occurring and possess many. Synthesis and reactions of benzofuran and benzothiophene. The diversityoriented synthetic route was also developed to allow facile access to bpbfs with a. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds. A facile and inexpensive synthesis of a series of novel methylenedioxybearing 2benzofuran2ylquinoline3carboxylic acid derivatives 3ah via the onepot reaction of ethyl 2chloromethyl6,7methylenedioxyquinoline3carboxylate 5 with various substituted salicylaldehydes 6ag as well as 2hydroxy1naphthaldehyde 6h is described substrate 5 was synthesized by the. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. The present invention relates to a process for the generation of a plurality of different benzofuran derivatives, and to the use of said benzofuran derivatives to search for novel classes of compounds and individual compounds possessing selected properties for pharmaceutical applications.
An efficient synthesis of benzofuran derivatives under conventionalnon. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. Psoralen is a furocoumarin compound formed by fusion of furan with coumarin, which is naturally exists in some. The possible mechanism of the novel rearrangement was also discussed. Furthermore, the 2methylbenzofuran derivatives 9 were synthesized using. These compounds are important intermediates for the synthesis of a variety of synthetically. Dec 27, 20 the synthesis of novel series of benzofuran derivatives, containing barbitone moiety, 524substitutedphenyl5substituted1benzofuran2yl methylidenepyrimidin2,4,61h,3h,5htrione 4ai and thiobarbitone moiety, 524substitutedphenyl5substituted1benzofuran2ylmethylidene2thioxodihydropyrimidin4,61h, 5hdione 5ai have been reported.
These products were synthesized starting with 2bromoacetylbenzofuran 1. The synthesis of novel series of benzofuran derivatives, containing barbitone moiety, 524substitutedphenyl5substituted1benzofuran2yl methylidenepyrimidin2,4,61h,3h,5htrione 4ai and thiobarbitone moiety, 524substitutedphenyl5substituted1benzofuran2ylmethylidene2thioxodihydropyrimidin4,61h, 5hdione 5ai have been reported. Synthesis of some benzofuran and furocoumarin derivatives for possible biological activity synthesis of some benzofuran and furocoumarin derivatives for possible biological activity hishmat, o. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. Realizing the importance of benzofuran derivatives in the synthesis of various drug sources reported in few classical methods such as, cyclocondensation of salicylaldehyde with. Synthesis of some benzofuran and furocoumarin derivatives. General procedure for the synthesis of n4oxothiazolidin3ylbenzofuran2carboxamide derivatives 6ag an equimolar mixture of schiff bases 4ae and thioacetic acid, and the catalytic amount of anhydrous zncl 2 was taken in dmf and refluxed for 68 h. The possible reaction mechanism for the formation of intermediate substituted phenanthro9,10b benzofuran and pyreno4,5b benzofuran is firstly depicted. Benzofuran as a promising scaffold for the synthesis of. The versatile reactivity of the trivalent phosphorus center of the parent bpbf offered access to a variety of derivatives by simple chemical modifications. The first scientific conference the collage of sciences 20 table2. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1. Moracins aez in medicinal chemistry ravi naik, dipesh s. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open.
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