Cn104870429b benzofuran derivative, preparation method. The benzofuran derivatives are naturally occurring and possess many biological applications. Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. Numerous approaches to these important compounds have been developed over the years but novel general procedures for their synthesis are still important. 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. Synthesis, characterization, antibacterial and antifungal properties of some novel benzofurans have been described. Benzofuran synthesis through iodocyclization reactions. Synthesis of benzofuran derivatives and their evaluation 637 synthesis of 2acetyl benzofuran 1 the mixture of salicylaldehyde 0.
Proof of their strucune was based mainly on 2dnmr as well as highresolution ms and cd experiments. Synthesis and biological activities of some benzofuran. Before joining jain university, he did his postdoctoral work at instituto superior tecnico. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and.
Synthesis of new derivatives of benzofuran as potential. Due to the presence of benzofuran moiety, they have a. 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. Synthesis and antimicrobial evaluation of new benzofuran derivatives. Sigmaaldrich offers a number of 2,3benzofuran products. As for the synthesis of benzofuran, mostly pericyclic reactions and transition. Synthesis of optically enriched spirocyclic benzofuran. 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. Benzofuran as a promising scaffold for the synthesis of. The turnoverlimiting step of the process was found to be co reductive elimination instead of ch activation. The successful use of various iodinating agents, bases, additives etc. Synthesis of difluoroalkylated benzofuran, benzothiophene, and. Novel benzofuran derivatives bearing naryl piperazine moiety.
Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. In this investigation, the synthesis of 2substituted pyrimidines by the reaction of. Synthesis of benzofuran pyrimidine derivatives 4ad, 5ad and 6ad. Synthesis and reactions of benzofuran and benzothiophene. Their in vitro antibacterial activities were evaluated against four types of bacteria and one fungus. 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. A novel strategy for the synthesis of benzofuran derivatives. 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. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. Synthesis of some benzofuran derivatives containing pyrimidine.
A practical, pd0pdiicatalyzed reaction was developed for phenoldirected ch activationco cyclization using air as an oxidant. A novel onepot threestep synthesis of 21benzofuran2yl. 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. Many naturally occurring benzofurans were also merged in drug design and. Mohammad shahidul islam, assem barakat, abdullah mohammed almajid, hazem a ghabbour, hoongkun fun and m. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring.
Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. The synthesis of a series of novel 1benzofuran2ylphenylmethylpyridine, imidazole, and triazole derivatives is described. Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1b inhibitor, bioorganic. 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. The present study deals with the synthesis of some substituted pyrazolines with. Synthesis of benzofuran derivatives and their evaluation of.
It may also be formed during other uses of coal or oil. 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. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds. Derivatives from tyrosol simple and efficient synthesis of. The hydrophobic benzofuran analogues exhibit favorable antibacterial activities, which were better than the positive control drugs. Synthesis and discovery and preliminary sar study of benzofuran derivatives as angiogenesis inhibitors reported by guochun zhuo10 kamal m. Design, synthesis, and biological evaluation of novel benzofuran derivatives bearing naryl piperazine moiety. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Pdf synthesis of some benzofuran derivatives containing. Rafiq siddiqui, stereoselective synthesis of diazaspiro5. Combining these considerations and the inspiration from keto alkyne. Usually these are called as benzofuran and isobenzofuran respectively figure 1. The cyclization of propargyl alcohols and amides gave oxazoles. Synthesis and biological evaluation of new benzofuran.
Synthesis and antimicrobial evaluation of new benzofuran. Benzofuran is the parent of many correlated compounds with more complex structures. Most of the synthesized benzofuran derivatives showed good. The reaction of 1ab with aryl isothiocyanates 2ah in chloroform as a solvent led to the formation of 3ah. Natural source, bioactivity and synthesis of benzofuran. 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. Furthermore, other benzofuran derivatives have been. Synthesis of benzofuran derivatives through cascade. The synthesis of the benzofuran derivatives is shown in scheme 1. Design, synthesis, and biological evaluation of novel benzofuran. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents. 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. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Antitubercular activity of benzofuran and naphthofuran derivatives.
Synthesis of oiododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. An efficient route to carbazoles and dibenzofurans has been developed. Synthesis of benzofuran derivatives and their evaluation. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed.
Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. 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. The present work describes the synthesis and characterization of six new dyes. 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. All the ligands were prepared for molecular docking by merging the nonpolar. In addition to the above, benzofuran derivatives possess a wide range of biological activities such as antimicrobial, antitumor, antiinflammatory 68. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. Onepot synthesis of novel symmetric 1,5dibenzofuran2.
Chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1benzofuran2yl derivatives. A novel onepot threestep synthesis of 21benzofuran2. Benzofuran derivatives are of special interest to natural product researchers for their biological activities and potential applications as. The synthesis and spectral properties of benzofuran. Benzofuran is the parent of many related compounds with more complex structures. 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. On the other hand, benzofuran derivatives are also present in many natural products 15 and exhibit properties like physiological, pharmacological, and toxic. Benzofuran is one of the most important classes of fused ring heterocyclic compounds.
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. Activity of benzofuran derivatives many benzofuran compounds, including those isolated from plants as well as obtained by synthesis, exhibit a variety of biological activity. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. The synthesis of the starting compound, 55hbr benzofuran2yl1phenyl1hpyrazole3carbohydrazides 1ab were achieved in quantitative yields by adopting published literature method. Benzofuran, benzothiophene, and indole derivatives are ubiquitous in bioactive. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. Synthesis of benzofuran derivatives via rearrangement and. Onepot synthesis protocol for highly functionalized. 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. This colourless solid is a component of the coal tar. Onepot synthesis protocol for highly functionalized benzofuran scaffold. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and.
A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. Synthesis and biological evaluations of some benzofuran. 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 of chalcone derivatives of benzo furan as.
Organothiosilanes in the synthesis of functionalized. Bioorganic and medicinal chemistry, bioorganic and medicinal chemistry 2009. Synthesis of sphenacylated trisubstituted 1,2,4triazole. 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. Pdf in this investigation, the synthesis of 2substituted pyrimidines by the reaction of benzofuran. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy.
In addition substituted benzofurans find application such. Synthesis, antimicrobial, and antioxidant activity of. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. 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. A number of optically enriched spirocyclic benzofuran. Karvekar, s andip patel and s ibaji sarkar nootan pharmacy college, s. Synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. School of dentistry at niigata, the nippon dental university, hamaura. Further it was planned to modify the carboxylic acid functionality by electron donor. The structure of this compound was determined as benzofuran derivative.
Organothiosilanes in the synthesis of functionalized benzothiophenes and benzofurans article in journal of sulfur chemistry 3034. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1. This reaction can tolerate a variety of functional groups and is complementary to the previous methods for the synthesis of substituted. It is well known that vitamin e having chroman skeleton have a. Synthesis of some benzofuran derivatives containing. For example, psoralen is a benzofuran derivative that occurs in several plants. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl. It is essentially prepared via alkaline hydrolysis of khellin, a natural furanochromone isolated from ammi visnaga l.
Pdf synthesis of derivatives of 4,5dihydrofuran, furan. In addition, benzofuran chalcone derivatives are foremost class of organic. Synthesis of new benzofuran2carboxylic acid derivatives. The first scientific conference the collage of sciences 20 synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. A novel strategy for the synthesis of benzofuran derivatives article in chinese journal of organic chemistry 3210. 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. 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. Synthesis of dibenzofurans via palladiumcatalyzed phenol. Highlights we synthesized a new series of benzofuran analogues with aryl substituents at its c2 and c3 positions. Institute of biology and molecular patologies ibpm, department of. Methods for the synthesis of benzofuran derivatives. Aryl benzofuran derivatives and oligostilbene derivatives. 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. Synthesis and pharmacological examination of benzofuran.
Synthesis of derivatives of 4,5dihydrofuran, furan, and hexahydrobenzofuran from conjugated alkenynes. First synthesis of 2benzofuran2yl6,7methylene dioxyquinoline3carboxylic acid derivatives wentao gao, jia liu, yun jiang and yang li. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial. We have discussed here significant biological properties of these derivatives such as antitumor, antimicrobial, antihyperglycemic, analgesic, antiinflammatory, antiviral, antipyretic activities etc. Angelicin, psoralen and bergapten are the examples of naturally occurring benzofuran derivatives with biological applications 46 fig. Dec 27, 20 chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1 benzofuran 2yl derivatives. Journal of chemical and pharmaceutical research, 2017, 95.
Synthesis and characterization of some new pyrazoline. 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. Postdoc journal journal of postdoctoral research vol. 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. Pnre comljounds either as the free phenols, the methyl ether, or the methyl etheracetate derivatives were isolated by a variety of. The literature shows that compounds with benzofuran nucleus have a wide. Over the past few decades, intramolecular cyclization leading to the synthesis of biologically relevant heterocyclic compounds has gained much attention as. First synthesis of 2 benzofuran 2yl6,7methylene dioxyquinoline3carboxylic acid derivatives wentao gao, jia liu, yun jiang and yang li. An efficient method for the synthesis of dibenzofurans from oiododiaryl ethers is catalyzed by reusable pdc under ligandfree conditions. Synthesis of some benzofuran derivatives containing pyrimidine moiety as. Benzofuran article about benzofuran by the free dictionary.