The excess dmf was distilled off and the reaction mixture was poured into ice. Synthesis and biological activities of some benzofuran derivatives with 4thiazolidinone moiety a b s t r a c t benzofurans are very interesting heterocycles, which are available in nature and show a wide range of pharmacological activities. Our goal was to obtain a small library of new, less lipophilic derivativesanalogs of lead compounds viiix. These compounds are important intermediates for the synthesis of a variety of synthetically useful and novel heterocyclic systems.
The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Synthesis of benzofuran derivatives through cascade. Derivatives from tyrosol simple and efficient synthesis of. Moracins aez in medicinal chemistry ravi naik, dipesh s. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction.
Novel benzofuran derivatives bearing naryl piperazine moiety. The possible mechanism of the novel rearrangement was also discussed. Some of the synthesized compounds were tested for in vitro. Synthesis of benzofuran derivatives and their evaluation.
Synthesis, characterization, and anticancer activity of. Substituted benzofurans also posses other applications such as fluorescent sensor, antioxidants, oxidant, brightening agents and in other field of chemistry and agriculture. Synthesis and biological activities of some benzofuran. Natural source, bioactivity and synthesis of benzofuran derivatives article pdf available in rsc advances 947. Synthesis and anticancer activity evaluation of new. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A series of substituted benzofuran derivatives were synthesized and characterized by spectral data. The synthesis and antimicrobial activity of some novel 11benzofuran2yl2mesitylethanone 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. Synthesis of some mannich bases and novel benzofuran derivatives containing imidazo2,1b1,3,4thiadiazoles as biological agents volume. Synthesis and antimicrobial evaluation of new benzofuran.
Design, synthesis and evaluation of benzofuranacetamide. Synthesis of benzofuran derivatives via different methods taylor. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Design, synthesis, and biological evaluation of novel benzofuran. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. Synthesis of chalcone derivatives of benzo furan as. Natural source, bioactivity and synthesis of benzofuran. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives 23, 27, and 28, respectively.
These products were synthesized starting with 2bromoacetylbenzofuran 1. This chloroacetylbenzofuran on treatment with urea in ethanol gives 4 1benzofuran2yl 1, 3oxazole2amine. Synthesis of elaborate benzofuran2carboxamide derivatives. 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. The versatile reactivity of the trivalent phosphorus center of the parent bpbf offered access to a variety of derivatives by simple chemical modifications. The corresponding compound on treatment with various aldehydes to give different derivative. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. Basepromoted onepot sequential oallylation of ohydroxycinnamates or cinnamonitrile or chalcones with. Synthesis and studying of antimicrobial and antioxidant. 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 properties of 4 were examined under various conditions. 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. Pdf a facile electrochemical method for synthesis of new.
Us7015246b2 us10471,444 us47144404a us7015246b2 us 7015246 b2 us7015246 b2 us 7015246b2 us 47144404 a us47144404 a us 47144404a us 7015246 b2 us7015246 b2 us 7015246b2 authority us united states prior art keywords hydrogen alkyl group optionally substituted halogen prior art date 20010329 legal status the legal status is an assumption and is not a legal. Realizing the importance of benzofuran derivatives in the synthesis of various drug sources reported in few classical methods such as, cyclocondensation of salicylaldehyde with. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. Unlimited viewing of the articlechapter pdf and any associated supplements and figures. Benzofuran derivatives from alkynylsubstituted benzynes.
Goldiiicatalyzed tandem reaction of oarylhydroxylamines with 1,3dicarbonyl compounds. Department of studies and research in industrial chemistry, jnana sahyadri, kuvempu university, shankaraghatta 577 451, shivmoga district, karnataka, india. Benzofuran synthesis through iodocyclization reactions. A cooperative pdcucatalyzed dual ch bond activation of electrondeficient polyfluoroarenes with aryl halides is developed. Design, synthesis and evaluation of benzofuran acetamide scaffold as potential anticonvulsant agent ashok k. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. Synthesis and cytotoxic activity against a nonsmallcell. An efficient synthesis of benzofuran derivatives under conventionalnon conventional method suryakant b. Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. The literature shows that compounds with benzofuran nucleus have a wide. Onepot allylationintramolecular vinylogous michael addition. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed.
The successful use of various iodinating agents, bases, additives etc. Synthesis of benzofuran derivatives and their evaluation of. The journal of organic chemistry 2010, 75 18, 63006303. The three patterns of reactivity observed for the o. Synthesis and biological evaluation of new benzofuran. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1. An efficient synthesis of benzofuran derivatives under. Furthermore, these continuous reactions could be achieved. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. In addition substituted benzofurans find application such. Pdf an efficient synthesis of benzofuran derivatives. Dubois, synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth, bioorg.
These synthesized compounds were screened for in vivo anticancer activity. Breaking the aromatic systems of electronrich arenes or heteroarenes provides threedimensional chemicals of high added value 1,2,3,4,5,6,7. Shin, microwaveassisted parallel synthesis of benzofuran2carboxamide derivatives bearing antiinflammatory, analgesic and antipyretic agents, tetrahedron lett. Synthesis, anticancer and molecular docking studies of. It is the parent of many related compounds with more complex structures. Benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Synthesis of benzofuran derivatives and their evaluation 637 synthesis of 2acetyl benzofuran 1 the mixture of salicylaldehyde 0. Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent ashok k. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. Methods for the synthesis of benzofuran derivatives.
Pdf synthesis of benzofuran derivatives and their evaluation of. A facile electrochemical method for synthesis of new benzofuran derivatives. Compounds 5s, 5r and 17b displayed the highest anticancer activity against ehrlich ascites. The benzofuran scaffold is a heterocyclic motif that consists of a fused benzene and furan ring, and many different synthetic strategies have been used in the past to introduce substituents on these two parts scheme 1a,b 8,9,10. Pdf a series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were. Electrooxidation enables highly regioselective dearomative. The final compounds were obtained in multistep synthesis reactions using benzofuranon3one derivatives a1a4, bas. Synthesis of new benzofuran2carboxylic acid derivatives. 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. Today, a large number of benzofuranbased drugs are available on the market, including examples such as methoxsalen that is used against psoriasis and eczema, the antiarrhythmic medications amiodarone and dronedarone, as.
All the newly synthesized compounds were confirmed by spectral studies. Synthesis, antimicrobial, and antioxidant activity of. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy.
Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. A unique intramolecular vinylogous michael addition leading to the synthesis of heterocycles has been disclosed. Onepot allylationintramolecular vinylogous michael. For example, psoralen is a benzofuran derivative that occurs in several plants. Benzofuran is maillard produced present in roasted coffee aroma. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. A palladium0catalyzed cascade reaction for the efficient synthesis of 2,3disubstituted benzofuran derivatives 3 containing a 3trisubstituted alkene functional group in moderate yields from alkynylsubstituted benzynes 1 and aryl halides 2 has been developed. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad. 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.
Benzophospholo3,2b benzofuran bpbf derivatives were studied as a new family of phospholecontaining. Synthesis of benzofuran derivatives through cascade radical. Pdf an efficient synthesis of benzofuran derivatives under. Benzofuran is the parent of many related compounds with more complex structures. General procedure for synthesis of benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran2carboxylic acid ethyl esters 2a or 2b 0. Synthesis and pharmacological activities of pyrazole. We designed the synthesis of a set of compounds containing a carboxyl 1, formamide 1a, and methoxycarbonyl groups 1b, instead of an acetyl group in the position 2 of the parent benzofuran ring to obtain new benzofuran viii analogs. In this study, we have synthesized 23 or 42aryl2oxoethoxyarylidenebenzofuran3one derivatives d1d38 and evaluated their anticancer activities. 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.
Synthesis of benzofuran derivatives via rearrangement and. A novel series of chalcones, 3aryl15bromo1benzofuran. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in largescale synthesis under oxidantfree conditions. Highly selective synthesis of 3carbonylated benzofuran derivatives. Synthesis and cytotoxic activity against a nonsmallcell bronchopulmonary carcinoma line nsclcn6 of benzofuran enantiomeric derivatives j. Us5919955a combinatorial solid phase synthesis of a. Moreover, compounds containing methanone linker between the aromatic rings and benzofuran at the c3 position had been investigated and reported as a uricosuricagent, a vasodilator, and a selective estrogen receptor modulator, such as benzbromarone and raloxifene fig. Salicylaldehyde upon treatment with chloroacetone in presence of anhydrous potassium carbonate give 2acetylbenzofuran. The structures of all compounds were established on the basis of analytical and spectral data. The diversityoriented synthetic route was also developed to allow facile access to bpbfs with a.
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. 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. Synthesis of some mannich bases and novel benzofuran. This protocol provides a unique and strategically distinct access to a variety of polyfluoroarenesubstituted benzofuran derivatives. The first group involves the formation of an annellated heterocyclic ring in this case furan by the intramolecular cyclization of benzene derivatives. Synthesis of new derivatives of benzofuran as potential. Aryl benzofuran derivatives and oligostilbene derivatives. Synthesis of polyfluoroarenesubstituted benzofuran. The anticancer activities of novel synthesized derivatives were evaluated against human lung cancer cell. For example, compound a 11, compound b 12 and compound c have been synthesized and evaluated as potent antitumor agents figure 1. A series of novel benzofuran scaffolds of amino pyrimidines 5a5s and azetidinones 17a17j were synthesized as potent biheterocyclic molecules. The synthesis and antimicrobial activity of some novel 11benzofuran2yl2 mesitylethanone derivatives eur. Koca m, sevi s, kirilmis c, kazaz c, ozbek b, et al. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans.
Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives. Review on synthetic routes for synthesis of benzofuranbased. 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. 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. Journal of chemical and pharmaceutical research, 2017, 95. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Synthesis, characterization, and anticancer activity of new. Us5919955a combinatorial solid phase synthesis of a library. A novel series of chalcones, 3aryl15bromo1 benzofuran.
Pdf natural source, bioactivity and synthesis of benzofuran. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. 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. Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. This 2acetylbenzzofuran after chlorination gives chloroacetylbenzofuran. Activity of benzofuran derivatives many benzofuran compounds, including those isolated from plants as well as obtained by synthesis, exhibit a variety of biological activity.
252 407 90 1503 1352 298 1532 978 1520 204 1539 150 498 783 601 869 1046 1550 914 500 1090 13 1609 53 692 743 276 1014 415 1149 1440 516 347 914 1102 792 292