Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. Read synthesis and antimicrobial evaluation of new benzofuran derivatives, european journal of medicinal chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. Their in vitro antibacterial activities were evaluated against four types of bacteria and one fungus. Synthesis, antimicrobial, and antioxidant activity of. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Benzofuran synthesis through iodocyclization reactions. Journal of chemical and pharmaceutical research, 2017, 95. It is well known that vitamin e having chroman skeleton have a.
Synthesis of benzofuran pyrimidine derivatives 4ad, 5ad and 6ad. Furthermore, other benzofuran derivatives have been. Benzofuran article about benzofuran by the free dictionary. School of dentistry at niigata, the nippon dental university, hamaura. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings.
Synthesis of some benzofuran derivatives containing pyrimidine. 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. Dec 27, 20 chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1 benzofuran 2yl derivatives. The key intermediate 4hydroxy6methylcoumarin b was prepared from pcresol and malonic acid using zncl2 as the catalyst in pocl3 and the mixture was stirred at 60 c for 24 h to give b. Synthesis of oiododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. Mohammad shahidul islam, assem barakat, abdullah mohammed almajid, hazem a ghabbour, hoongkun fun and m. Synthesis and biological activities of some benzofuran. Synthesis of new derivatives of benzofuran as potential. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Synthesis of some benzofuran derivatives containing. The synthesis of the starting compound, 55hbr benzofuran2yl1phenyl1hpyrazole3carbohydrazides 1ab were achieved in quantitative yields by adopting published literature method.
Rafiq siddiqui, stereoselective synthesis of diazaspiro5. Design, synthesis, and biological evaluation of novel benzofuran derivatives bearing naryl piperazine moiety. The literature shows that compounds with benzofuran nucleus have a wide. Znotf 2 catalyzed the cyclization of propargyl alcohols with anilines and phenols in toluene at 100c without additive and gave various indole and benzofuran products with different structures. Chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1benzofuran2yl derivatives. Natural source, bioactivity and synthesis of benzofuran. A novel onepot threestep synthesis of 21benzofuran2yl. Proof of their strucune was based mainly on 2dnmr as well as highresolution ms and cd experiments. The cyclization of propargyl alcohols and amides gave oxazoles.
Design, synthesis, and biological evaluation of novel benzofuran. Synthesis of optically enriched spirocyclic benzofuran. Aug 01, 2011 read synthesis and antimicrobial evaluation of new benzofuran derivatives, european journal of medicinal chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Synthesis and discovery and preliminary sar study of benzofuran derivatives as angiogenesis inhibitors reported by guochun zhuo10 kamal m. Organothiosilanes in the synthesis of functionalized benzothiophenes and benzofurans article in journal of sulfur chemistry 3034. Michael addition reaction of substituted benzofuran. Benzofuran is the parent of many correlated compounds with more complex structures. Synthesis and antimicrobial evaluation of new benzofuran. Initially the two derivatives of 21benzofuran2yl quinoline4carboxylic acid 3ab were synthesized, and it was found that they emit light in the blue region of the spectrum. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. A novel strategy for the synthesis of benzofuran derivatives article in chinese journal of organic chemistry 3210. Pdf in this investigation, the synthesis of 2substituted pyrimidines by the reaction of benzofuran.
Synthesis of benzofuran derivatives and their evaluation. A novel strategy for the synthesis of benzofuran derivatives. 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. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring.
Benzofuran derivatives are of special interest to natural product researchers for their biological activities and potential applications as. Synthesis of benzofuran derivatives via rearrangement and. Karvekar, s andip patel and s ibaji sarkar nootan pharmacy college, s. Onepot synthesis protocol for highly functionalized. Synthesis of derivatives of 4,5dihydrofuran, furan, and hexahydrobenzofuran from conjugated alkenynes.
Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. Novel benzofuran derivatives bearing naryl piperazine moiety. Highlights we synthesized a new series of benzofuran analogues with aryl substituents at its c2 and c3 positions. As for the synthesis of benzofuran, mostly pericyclic reactions and transition. Synthesis of some benzofuran derivatives containing pyrimidine moiety as. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives. Synthesis of dibenzofurans via palladiumcatalyzed phenol. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. An efficient route to carbazoles and dibenzofurans has been developed. They also display many applications like sedatives, antioxidants 16, pharmaceuticals 17 20, cosmetics 21, molecular switches 22, 23, and also for the building blocks of optical. The obtained ethyl halo benzofuran 2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride when this process was carried out in boiling methanol for 16 hours the target benzofuran 2carboxylic acid 2hydroxy1,1dimethylethylamides 3a and 3b were obtained in moderate yi. The reaction of 1ab with aryl isothiocyanates 2ah in chloroform as a solvent led to the formation of 3ah. Benzofuran is the parent of many related compounds with more complex structures.
This colourless solid is a component of the coal tar. A facile and efficient onepot threestep procedure for the preparation of 21benzofuran2ylquinoline3carboxylic 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. It is essentially prepared via alkaline hydrolysis of khellin, a natural furanochromone isolated from ammi visnaga l. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. Synthesis and pharmacological examination of benzofuran. Numerous approaches to these important compounds have been developed over the years but novel general procedures for their synthesis are still important.
Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. The benzofuran derivatives are naturally occurring and possess many biological applications. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. Benzofuran is one of the most important classes of fused ring heterocyclic compounds. Antitubercular activity of benzofuran and naphthofuran derivatives. The reported synthesis starting from 1trimethylsilyl1,3 butadiyne a 31 and protected 2iodophenol b, we have realized the synthesis of several orthosubstituted aryl diynes c,which produce various benzofuran derivatives. In addition, benzofuran chalcone derivatives are foremost class of organic. Methods for the synthesis of benzofuran derivatives.
Institute of biology and molecular patologies ibpm, department of. In this investigation, the synthesis of 2substituted pyrimidines by the reaction of. All the ligands were prepared for molecular docking by merging the nonpolar. The synthesis of the benzofuran derivatives is shown in scheme 1. The structure of this compound was determined as benzofuran derivative. Benzofuran, benzothiophene, and indole derivatives are ubiquitous in bioactive. First synthesis of 2 benzofuran 2yl6,7methylene dioxyquinoline3carboxylic acid derivatives wentao gao, jia liu, yun jiang and yang li. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans.
Sigmaaldrich offers a number of 2,3benzofuran products. The synthesis of a series of novel 1benzofuran2ylphenylmethylpyridine, imidazole, and triazole derivatives is described. Synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. Synthesis of benzofuran derivatives through cascade. Nov 19, 2010 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.
Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. Bioorganic and medicinal chemistry, bioorganic and medicinal chemistry 2009. Further it was planned to modify the carboxylic acid functionality by electron donor. Pdf synthesis of some benzofuran derivatives containing. Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1b inhibitor, bioorganic. Derivatives from tyrosol simple and efficient synthesis of. In addition substituted benzofurans find application such. Synthesis of sphenacylated trisubstituted 1,2,4triazole. The present invention relates to a kind of benzofuran derivatives, its preparation method and its in application pharmaceutically, and in particular to one plant the novel benzofuran derivatives with g protein coupled receptor 40 gpr40 function of receptors adjustment effect or its solid is different structure body, hydrate, solvate, eutectic. 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 first scientific conference the collage of sciences 20 synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial.
The present study deals with the synthesis of some substituted pyrazolines with. Activity of benzofuran derivatives many benzofuran compounds, including those isolated from plants as well as obtained by synthesis, exhibit a variety of biological activity. Synthesis of benzofuran derivatives and their evaluation of. Benzofuran as a promising scaffold for the synthesis of. Before joining jain university, he did his postdoctoral work at instituto superior tecnico. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. Combining these considerations and the inspiration from keto alkyne. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds.
The hydrophobic benzofuran analogues exhibit favorable antibacterial activities, which were better than the positive control drugs. Synthesis and biological evaluations of some benzofuran. Onepot synthesis of novel symmetric 1,5dibenzofuran2. Synthesis of benzofuran derivatives and their evaluation 637 synthesis of 2acetyl benzofuran 1 the mixture of salicylaldehyde 0. 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. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Onepot synthesis protocol for highly functionalized benzofuran scaffold. 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. Over the past few decades, intramolecular cyclization leading to the synthesis of biologically relevant heterocyclic compounds has gained much attention as. Synthesis, characterization, antibacterial and antifungal properties of some novel benzofurans have been described. Postdoc journal journal of postdoctoral research vol. Initially the two derivatives of 21 benzofuran 2yl quinoline4carboxylic acid 3ab were synthesized, and it was found that they emit light in the blue region of the spectrum.
This article is covered the methods of synthesis of benzofuran and its derivatives, structural activity relationship and pharmacological activities so it is an effort to highlight the importance of the benzofuran in the present context and promise they hold for the future. First synthesis of 2benzofuran2yl6,7methylene dioxyquinoline3carboxylic acid derivatives wentao gao, jia liu, yun jiang and yang li. In addition to the above, benzofuran derivatives possess a wide range of biological activities such as antimicrobial, antitumor, antiinflammatory 68. For example, psoralen is a benzofuran derivative that occurs in several plants. 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 5.
Synthesis and antimicrobial evaluation of new benzofuran derivatives. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Due to the presence of benzofuran moiety, they have a. Synthesis of new benzofuran2carboxylic acid derivatives. The synthesis and spectral properties of benzofuran. Organothiosilanes in the synthesis of functionalized.
Many naturally occurring benzofurans were also merged in drug design and. The successful use of various iodinating agents, bases, additives etc. 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. A novel onepot threestep synthesis of 21benzofuran2. 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. Angelicin, psoralen and bergapten are the examples of naturally occurring benzofuran derivatives with biological applications 46 fig. 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. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1.
A number of optically enriched spirocyclic benzofuran. It may also be formed during other uses of coal or oil. On the other hand, benzofuran derivatives are also present in many natural products 15 and exhibit properties like physiological, pharmacological, and toxic. 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.
Synthesis of chalcone derivatives of benzo furan as. A practical, pd0pdiicatalyzed reaction was developed for phenoldirected ch activationco cyclization using air as an oxidant. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Cn104870429b benzofuran derivative, preparation method. 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. We have discussed here significant biological properties of these derivatives such as antitumor, antimicrobial, antihyperglycemic, analgesic, antiinflammatory, antiviral, antipyretic activities etc. The turnoverlimiting step of the process was found to be co reductive elimination instead of ch activation. Synthesis and reactions of benzofuran and benzothiophene. Synthesis and biological evaluation of new benzofuran. An efficient method for the synthesis of dibenzofurans from oiododiaryl ethers is catalyzed by reusable pdc under ligandfree conditions. Pnre comljounds either as the free phenols, the methyl ether, or the methyl etheracetate derivatives were isolated by a variety of.
Aryl benzofuran derivatives and oligostilbene derivatives. Most of the synthesized benzofuran derivatives showed good. Pdf synthesis of derivatives of 4,5dihydrofuran, furan. Synthesis of difluoroalkylated benzofuran, benzothiophene, and. This reaction can tolerate a variety of functional groups and is complementary to the previous methods for the synthesis of substituted. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. The present work describes the synthesis and characterization of six new dyes. Synthesis and characterization of some new pyrazoline.