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 new compounds were identified as 9rmoracin p 3. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. A series of novel benzofuran carboxylic acid derivatives have been designed and synthesized, with their antagonism effect screened on et1induced contraction in the rat thoracic aortic ring. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. These are only a few examples from a large group of benzofurans with anticancer activity. All the natural phosphodonors acetyl phosphate, carbamoyl phosphate, phosphoramidate, and monophosphoimidazole bind to active site with binding. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Pdf synthesis of benzofuran derivatives and their evaluation of. Benzofuran synthesis through iodocyclization reactions. 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.
Four new benzofurantype stilbene glycosides and 14 known compounds including 8 benzofurantype stilbenes and 6 flavonoids were isolated from the traditional chinese medicine, cortex mori radicis. Benzofurans heterocyclic building blocks sigmaaldrich. Benzofuran is maillard produced present in roasted coffee aroma. Some of these synthesized compounds were evaluated for cytotoxicity activity against hepg2 liver carcinoma cell line and hela cervix carcinoma cell. In view of the literature survey of benzofuran as a pharmacological agent and on preparation of 1,5dicarbonyl derivatives, here in the present work we report on one pot synthesis of novel symmetric 1,5dibenzofuran2yl34substitutedarylpentane1,5dione derivatives under solvent free condition.
Onepot synthesis of novel symmetric 1,5dibenzofuran2. A diversity of synthetic routes can be applied to the synthesis of benzofurans. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. The present invention provides a benzofuran derivative of the formula 1. In silico antitubercular activity analysis of benzofuran.
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. Synthesis and cytotoxicity screening of some novel. The benzofuran derivatives are naturally occurring and possess many. Benzofuran is the parent of many related compounds with more complex structures. This study reports that a novel phenolic benzofuran derivative could be obtained selectively from g1 by further alkaline treatment. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Benzofuran derivatives patent us2009209511 pubchem. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications.
Novel benzofuran derivatives bearing naryl piperazine moiety. Using the conditions established for cicerfurane16, 6 was. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. The structure of the synthesized compounds was elucidated by ir, 1 h nmr, mass spectral data and elemental analysis. Benzofuran derivatives as tubulin polymerization inhibitors ref. Department of studies and research in industrial chemistry, jnana sahyadri, kuvempu university, shankaraghatta 577 451, shivmoga district, karnataka, india.
For example, psoralen is a benzofuran derivative that occurs in several plants. Derivatives from tyrosol simple and efficient synthesis of. The structure of this compound was determined as benzofuran derivative. Onepot formation of functionalized indole and benzofuran derivatives using a single bifunctional ruthenium catalyst by reji n. A phytochemical investigation of the root of angelica dahurica led to the isolation of benzofuran and coumarin derivatives. A previous literature survey described a variety of 2 substituted benzofuran derivatives that received a great deal of attention for their antihiv18,9,10,11, anticancer11,12,14,15, and antimicrobial11,16,17,18, activities. Given the vast number of applications of benzofuranbased drugs in todays medicine, there exists considerable interest for novel synthetic methodologies that can grant expedient access to new kinds of. Synthesis of benzofuran derivatives through cascade. The structural data of all benzofuran derivatives is shown in table 1. Synthesis of some mannich bases and novel benzofuran derivatives containing imidazo2,1b1,3,4thiadiazoles as biological agents volume. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Synthesis of some mannich bases and novel benzofuran.
A series of new pyrazole, thiazole and thiazolinone derivatives incorporated into benzofuran were synthesized by using 3benzofuran2yl1phenyl1hpyrazol4carboxaldehyde as starting material. It is well known that vitamin e having chroman skeleton have a. Benzofuran definition of benzofuran by the free dictionary. We report a single bifunctional ruthenium catalyst for cyclization of terminal alkynylaryl amines and phenols to corresponding indole and benzofuran derivatives in good yields. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. Natural source, bioactivity and synthesis of benzofuran derivatives. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride.
Usually these are called as benzofuran and isobenzofuran respectively figure 1. Some of the synthesized compounds were tested for in vitro. Furthermore, other benzofuran derivatives have been shown to display a wide range of antimicrobial and anticancer properties 1,2,3,4,5,6,7. In this chapter, the biological activities of several synthetic and naturally occurring substituted benzofuran derivatives are reported. Benzofuran is one of the most important classes of fused ring heterocyclic compounds. 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. Benzofuran definition and meaning collins english dictionary. Benzofuran derivatives are often applied to medical use, antiseptic, pesticide, fuel additive and so on.
Synthesis of benzofuran derivatives via different methods taylor. These compounds are important intermediates for the synthesis of a variety of synthetically useful and novel heterocyclic systems. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. An efficient synthesis of benzofuran derivatives under. It is the parent of many related compounds with more complex structures. 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.
Natural source, bioactivity and synthesis of benzofuran derivatives article pdf available in rsc advances 947. The structures of these compounds were established by extensive analysis of 1d2d nmr data, mass spectrometric data, and optical rotation or. Results and discussion the first set of experiments was directed towards the onepot protectioncouplingcyclization of bromohydroquinone 6, figure 3. Benzofurans are chemical compounds which contain a benzofuran ring in their structure. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with biological and pharmacological potentials. Herein, the series of benzofuran derivatives have been prepared by applying the methods mentioned above. Furthermore, recent studies showed that benzofuran ring system fused with heterocyclic moieties exhibit a wide spec.
The structures of a total of twelve undescribed compounds were determined by extensive spectroscopic analysis, including 2d nmr data, hydrolysis, and solvolysis, followed by either physicochemical and spectroscopic data or xray crystallographic analysis. Three new prenylated phenol derivatives, terreprenphenols ac, along with four known related compounds 47, were isolated from aspergillus terreus en539, an endophytic fungus obtained from the marine red alga laurencia okamurai. Benzofuran biodegraded using a enriched culture from a creosote contaminated site1 where biodegradation of benzofuran was enhanced by the degradation of other creosote compounds1. Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. In addition substituted benzofurans find application such. Benzofuran core is a highly versatile and of great medicinal interest due to its presence in many natural products. Benzofuran was completely removed in combination with toluene, pxylene, mxylene, naphthalene, 1methylnapthalene within the first 12 days of incubation, compared with a 7% loss in the acidified control microcosm1. Journal of chemical and pharmaceutical research, 2017, 95. A series of novel hybrid compounds between benzofuran and naryl piperazine have been synthesized. Onepot formation of functionalized indole and benzofuran derivatives using a single bifunctional ruthenium catalyst.
Theresa may mp, home secretary home office 2 marsham street london sw1p 4df 28 november 20 dear home secretary, in may 20, the acmd advised that the synthetic benzofuran series of chemicals. Suggested production of a guaiacyl benzofuran derivative. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Y is an optionally substituted amino group, an optionally substituted cycloalkyl group or an optionally substituted saturated heterocyclic group. Design, synthesis and evaluation of benzofuranacetamide. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. A is a single bond, a carbon chain optionally having a double bond within or at the ends of the chain, or an oxygen atom. Reactivity of benzofuran derivatives article pdf available in synthetic communications 4420 october 2014 with 2,217 reads how we measure reads. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. A series of substituted benzofuran derivatives were synthesized and characterized by spectral data. An international journal for rapid communication of synthetic organic chemistry, 44. The production mechanism and a parallel occurring reaction were also demonstrated. Synthesis of benzofuran derivatives and their evaluation of.
A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. The first group involves the formation of an annellated heterocyclic ring in this case furan by the intramolecular cyclization of benzene derivatives. The in silico interaction of phosphodonors to narl was carried out and it was observed that all compounds were binding to active site, though blind docking was performed. Naturally benzofuran derivatives can be isolated from various medicinal plants and marine products. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad. Scheme 1 illustrates the preparation of target compounds. Owing to these biological activities and potential applications in many aspects, benzofuran compounds have attracted more and more attention of. Benzofuran derivatives from alkynylsubstituted benzynes. Synthesis of chalcone derivatives of benzo furan as. The successful use of various iodinating agents, bases, additives etc. A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes. 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. Antitubercular activity study of benzofuran and naphthofuran derivatives. Supporting information fluorinated benzofuran derivatives.
Benzofuran and coumarin derivatives from the root of. Synthesis and hplc method validation of novel 3fluoron7methoxy24methoxyphenyl1benzofuran5ylmethylaniline on free shipping on qualified orders. 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. Design, synthesis, and biological evaluation of benzofuran. In addition substituted benzofurans find application such as of fluorescent sensor 17, oxidant 18, antioxidants, brightening agents, a variety of drugs and in. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. The derivatives of keto benzofuran are useful as medicines, such as amiodarone and benziodarone, particulary for. Synthesis of new benzofuran2carboxylic acid derivatives. Synthesis and biological activities of some benzofuran. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized.
Some target compounds demonstrated significant inhibitory activity, especially benzo c thiadiazole and benzo c oxadiazole compounds 29 and 30 showed. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. Methods for the synthesis of benzofuran derivatives. Onepot formation of functionalized indole and benzofuran. Bioactive benzofuran derivatives from cortex mori radicis. Key features the ability to cyclize and hydrate terminal alkynes in one step and to deuterate the heteroaromatic compounds formed. Some physiological properties of benzofuran and dibenzofuran derivatives earl westley smith iowa state college follow this and additional works at. Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent ashok k. Design, synthesis, and biological evaluation of novel benzofuran. Pdf reactivity of benzofuran derivatives researchgate.
School of dentistry at niigata, the nippon dental university, hamaura. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Synthesis of new derivatives of benzofuran as potential. This is the first report of the isolation and identification of three furanocoumarin sulfates from a. Benzofuran derivatives display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor, activities. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct.
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