Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial. Benzofuran derivatives display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor, activities. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. The invention is directed to methods to inhibit p38.
Benzofuran as a promising scaffold for the synthesis of. Antitubercular activity of benzofuran and naphthofuran derivatives. Synthesis and biological evaluations of some benzofuran derivatives riddhi madhu, m. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds. Synthesis and pharmacological examination of benzofuran. Synthesis of chalcone derivatives of benzo furan as. The synthesis and spectral properties of benzofuran. Benzofuran is maillard produced present in roasted coffee aroma. This approach is successfully applied in the first total synthesis of the natural product aspergillusene b.
Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5. Synthesis of benzofuran derivatives via rearrangement and. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. Synthesis and biological evaluations of some benzofuran. Synthesis of benzofuran derivatives via rearrangement and their inhibitory activity on acetylcholinesterase xiang zhou 1, miao li 2, xiaobing wang 1, tao wang 2 and lingyi kong 1, 1 department of natural medicinal chemistry, china pharmaceutical university, 24 tong jia xiang, nanjing 29, china. 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 benzofuran. Pdf synthesis of benzofuran derivatives and their evaluation of. Some target compounds demonstrated significant inhibitory activity, especially benzo c thiadiazole and benzo c oxadiazole compounds 29 and 30 showed. Palladium catalysis enables an intramolecular cyclisation of orthodiazonium salts of diaryl ethers to give dibenzofurans. Us20030158417a1 benzofuran derivatives as inhibitors of p38. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source.
Moreover, 7piperazinylbenzofuran2carbxylic acid amides having halogens or methoxyl groups in benzene ring were patented as partial agonists of 5ht receptors which should. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. The successful use of various iodinating agents, bases, additives etc. Abstract benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by. Due to the presence of benzofuran moiety, they have a. Pnre comljounds either as the free phenols, the methyl ether, or the methyl etheracetate derivatives were isolated by a variety of. The main example of the potentiality of this synthetic pathway for the preparation of compounds bearing the benzofuran skeleton is the easily and convenient transformation. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Some physiological properties of benzofuran and dibenzofuran. Ep0471609b1 benzofuran derivatives, benzothiophenes.
Pdf a series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were. H functionalizations using two different electrophiles are also reported to afford. Natural source, bioactivity and synthesis of benzofuran. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Benzofuran derivatives from alkynylsubstituted benzynes. Benzofuran synthesis through iodocyclization reactions.
Some physiological properties of benzofuran and dibenzofuran derivatives earl westley smith iowa state college follow this and additional works at. The protocol uses 3 mol% palladium acetate as the catalyst in refluxing ethanol in the absence of base. Pdf synthesis and biological activities of furan derivatives. An efficient synthesis of benzofuran derivatives under. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct.
A series of benzofuran derivatives were designed and synthesized, and their inhibitory activites were measured against the sirt. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Natural source, bioactivity and synthesis of benzofuran derivatives article pdf available in rsc advances 947. Synthesis and reactions of benzofuran and benzothiophene. In addition substituted benzofurans find application such as of fluorescent sensor 17, oxidant 18, antioxidants, brightening agents, a variety of drugs and in. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin.
We found that the substituted salicylaldehydes containing different functional groups i. Natural source, bioactivity and synthesis of benzofuran derivatives. Recently, in the process of new drug discovery, the anticancer and antiviral activities of a variety of benzofuran derivatives i 10, nsc725612 and nsc725616. An efficient homogeneous catalytic enantioselective synthesis of. Application of radical chemistry to solid support synthesis. A novel nonaromatic pool synthetic strategy for the synthesis of benzofuran based natural products via oxidative haloaromatization of enones is reported. Benzophospholo3,2b benzofuran bpbf derivatives were studied as a new family of phospholecontaining. Benzofuran is the parent of many related compounds with more complex structures. A novel onepot threestep synthesis of 21benzofuran2yl. Benzofuran, benzothiophene, and indole derivatives are ubiquitous in. Total synthesis of benzofuranbased aspergillusene b via.
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 1,5di benzofuran 2yl34substitutedarylpentane1,5dione derivatives under solvent free condition. Exposure to 2,3benzofuran is most likely to occur from breathing contaminated air at the workplace. 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. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six. The versatile reactivity of the trivalent phosphorus center of the parent bpbf offered access to a variety of derivatives by simple chemical modifications. Synthesis and biological activities of furan derivatives article pdf available in international journal of research in ayurveda and pharmacy 24. 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. Novel benzofuran derivatives bearing naryl piperazine moiety. Herein, the series of benzofuran derivatives have been prepared by applying the methods mentioned above. Synthesis of benzofuran derivatives on solid support via. In comparison with a separately executed aromatic pool synthesis, the nonaromatic pool protocol demonstrates. Synthesis andin vitro evaluation of some novel benzofuran. Derivatives from tyrosol simple and efficient synthesis of.
A facile and efficient onepot threestep procedure for the preparation of 21 benzofuran 2ylquinoline3carboxylic acid derivatives is described, featuring three different synthetic transformations, namely williamson ether synthesis, hydrolysis of an ester group at the quinoline ring c3 position, and intramolecular electrophilic cyclization reaction between the aldehyde group of. The mechanisms of the reactions and their use in t. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a. 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. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. The broad range of clinical uses of benzofuran derivatives indicate the diverse. Synthesis of benzofuran derivatives through cascade radical. Proof of their strucune was based mainly on 2dnmr as well as highresolution ms and cd experiments. General procedure, characterization data, 1h, c and 19f nmr spectra pdf. Synthesis of 15substituted benzofuran2yl3arylurea derivatives as antimicrobial agents. Agency for toxic substances and disease registry toxfaqs september 1995. An international journal for rapid communication of synthetic organic chemistry, 44.
Synthesis and evaluation of novel benzofuran derivatives. S1 supporting information synthesis and properties of benzophospholo3,2b benzofuran derivatives motonobu takahashi, koji nakano, kyoko nozaki department of chemistry and biotechnology, graduate school of engineering, the university of tokyo, 731 hongo, bunkyoku, tokyo 18656, japan. Journal of chemical and pharmaceutical research, 2017, 95. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl. Electrochemical synthesis of 5,6dihydroxy2methyl1 benzofuran 3carboxylate derivatives were reported by ali reza fakhari and his coworkers17 the synthesis and antimicrobial activity of some novel 11 benzofuran 2yl2mesitylethanone derivatives were reported by cumhur kirilmis et al18. Synthesis of difluoroalkylated benzofuran, benzothiophene, and.
Synthesis of benzofuran derivatives through cascade. 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. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. In silico antitubercular activity analysis of benzofuran and naphthofuran derivatives in the literature, there has not been enough work on the investigation of thermal degradation kinetics of methacrylate polymers with 5bromo benzofuran derivative so far. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. For example, psoralen is a benzofuran derivative that occurs in several plants.
Karvekar, s andip patel and s ibaji sarkar nootan pharmacy college, s. Design, synthesis, and biological evaluation of novel benzofuran. Supporting information synthesis and properties of. The derivatives of keto benzofuran are useful as medicines, such as amiodarone and benziodarone, particulary for. Synthesis andin vitro evaluation of some novel benzofuran derivatives as potential antihiv1, anticancer, and antimicrobial agents. Animal studies have shown effects on the liver, kidneys, lungs, and stomach from exposure to high levels of 2,3benzofuran. 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. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. 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. Sahakar vidyadham, kamana crossing, ambaji road, visnagar384315, india email. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. The diversityoriented synthetic route was also developed to allow facile access to bpbfs with a.
Synthesis of benzofuran derivatives and their evaluation of antimicrobial activity article pdf available in ejournal of chemistry 72 april 2010 with 600 reads how we measure reads. Benzofuran article about benzofuran by the free dictionary. Synthesis and biological activities of some benzofuran. Benzofuran is the parent of many correlated compounds with more complex structures. Synthesis and biological evaluation of new benzofuran. In addition substituted benzofurans find application such. Files available from the acs website may be downloaded for. Synthesis of new benzofuran2carboxylic acid derivatives. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Amide derivatives of halo benzofuran 2carboxylic acid were found to be useful in the treatment of the diseases which are associated with the modulation of h3 receptors.
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