Furthermore, scientists at roche have demonstrated that the pyrazolotriazine 69 template was a good replacement for indole in terms of 5ht 6. Design, synthesis, and biological evaluation of novel benzofuran. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Benzofuran article about benzofuran by the free dictionary. Benzofuran derivatives galileo pharmaceuticals, inc. Jan 02, 1990 2,3 benzofuran is a colorless, sweetsmelling, oily liquid which does not mix with water. Michael addition reaction of substituted benzofuran. Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. Pdf synthesis of some benzofuran derivatives containing. Benzofuran and its derivatives have attracted medicinal chemists and pharmacologists due to their pronounced biological activities and their potential applications.
Benzofuran derivatives display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor, activities. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. Synthesis and biological activities of some benzofuran. This study reports that a novel phenolic benzofuran derivative could be obtained selectively from g1 by further alkaline treatment. Most compounds showed a selective antibacterial activity to grampositive bacteria and four. Synthesis of some benzofuran derivatives containing pyrimidine. An efficient synthesis of benzofuran derivatives under. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Benzofuran derivatives are often applied to medical use, antiseptic, pesticide, fuel additive and so on. The part of the coal oil that contains 2,3benzofuran is made into a plastic called coumaroneindene resin. The docking score of benzofuran derivatives of ba series is ranging from 3. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials.
Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Synthesis of new derivatives of benzofuran as potential. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. The structure of this compound was determined as benzofuran derivative. The production mechanism and a parallel occurring reaction were also demonstrated. School of dentistry at niigata, the nippon dental university, hamaura. Onepot synthesis of novel symmetric 1,5dibenzofuran2. Jul 18, 2006 benzofuran derivatives, process for the preparation of the same and uses thereof. 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. Under no circumstances may this pdf file be placed on a network of any sort without our express permission. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy.
Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran.
Antitubercular activity of benzofuran and naphthofuran 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. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. Benzofuran is maillard produced present in roasted coffee aroma. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. Derivatives from tyrosol simple and efficient synthesis of.
Though there are many methodology are available for designing and developing newer drug. The derivatives of keto benzofuran are useful as medicines, such as amiodarone and benziodarone, particulary for. Solidstate emission enhancement via molecular engineering of benzofuran derivatives jere. Journal of chemical and pharmaceutical research, 2012, 4. Benzofuran derivatives have drawn considerable attention due to their. Benzofurane derivatives, preparation method, use as medicines and pharmaceutical compositions containing same. Synthesis of 2,3difunctionalized benzofuran derivatives through. Synthesis and discovery and preliminary sar study of benzofuran derivatives as angiogenesis inhibitors reported by guochun zhuo10. Rather, the part of the coal oil that contains 2,3 benzofuran is made into a plastic called coumaroneindene resin. The successful use of various iodinating agents, bases, additives etc. Journal of chemical and pharmaceutical research, 2017, 95. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings.
Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. Benzofuran derivatives, process for the preparation of the same and uses thereof. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. With this method, a large number of hydroxylated benzofuran derivatives with different substitution. Pdf in this investigation, the synthesis of 2substituted pyrimidines by the reaction of benzofuran. A series of novel hybrid compounds between benzofuran and naryl piperazine have been synthesized.
Researchers at biovitrum claimed a range of these benzofuran and benzothiophenebased derivatives 66 and 67 as 5ht 6 antagonists in several patent applications caldirola et al. Synthesis of chalcone derivatives of benzo furan as. A number of optically enriched spirocyclic benzofuran. 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. Benzofurans heterocyclic building blocks sigmaaldrich. 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. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. Benzofuran definition of benzofuran by the free dictionary. The part of the coal oil that contains 2,3 benzofuran is made into a plastic called coumaroneindene resin.
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. Certain benzofuran derivatives are useful in the treatment of certain ischemic or inflammatory conditions, as well as neuroinflammation, neurodegeneration or degenerative diseases in which mitochondrial dysfunction leads to tissue degeneration. All the ligands were prepared for molecular docking by merging the nonpolar. The docking score with 3fdn is maximum with bh3oh and minimum with ba4ch3. Benzofuran synthesis through iodocyclization reactions. An international journal for rapid communication of synthetic organic chemistry, 44. Herein, the series of benzofuran derivatives have been prepared by applying the methods mentioned above.
Synthesis of polyfunctionalized benzofurans via onepot domino. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. These are only a few examples from a large group of benzofurans with anticancer activity. Benzofuran as a promising scaffold for the synthesis of.
Synthesis of 2, 3difunctionalized benzofuran derivatives through. Suggested production of a guaiacyl benzofuran derivative. In addition substituted benzofurans find application such as of fluorescent sensor 17, oxidant 18, antioxidants, brightening agents, a variety of drugs and in. 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. Benzofurans are chemical compounds which contain a benzofuran ring in their structure.
Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. Synthesis of new benzofuran2carboxylic acid derivatives. 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. Moreover, 7piperazinylbenzofuran2carbxylic acid amides having halogens or methoxyl groups in benzene ring were patented as partial agonists of 5ht receptors which should. Synthesis and antimicrobial evaluation of 3substituted. 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. The derivatives of keto benzofuran are useful as medicines, such as amiodarone and benziodarone, particularly for the treatment of pathological syndromes of the cardiovascular system, such as arrhythmia 17. However, many synthetic halogen substituted benzofuran derivatives have been reported from our laboratory and found to possess wide range of biological and pharmacological activities such as antiviral, analeptic, antimicrobial, analgesic, and antiinflammatory.
Novel benzofuran derivatives bearing naryl piperazine moiety. The outstanding development of benzofuran derivatives in diverse diseases in very short span of time proves its magnitude for medicinal chemistry research. Some physiological properties of benzofuran and dibenzofuran derivatives earl westley smith iowa state college follow this and additional works at. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Synthesis and biological evaluation of new benzofuran. Onepot synthesis protocol for highly functionalized benzofuran scaffold preetpal s sidhu department of chemistry and biochemistry university of wisconsin, milwaukee, wi email. The key benzofuran analog 66 bvt74316 was recently reported to be in phase i development. The condensation of 1,4benzoquinone arylsulfonylimines with esters and arylamides of 3alkyl and 3cycloalkylaminocrotonic acids has been studied and the conditions for the cyclization of the resulting products into benzofuran derivatives are discussed. Benzofuran is the parent of many related compounds with more complex structures. The simple benzofuran derivatives like 2nitrobenzofuran 2, 2acetyl benzofurans are well known as biodynamic agents possessing various pharmacological properties i. The structures of all the newly synthesized compounds have been established by spectral studies. A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes.
Benzofuran derivatives are valuable structural motifs that are often found. A series of 3substitutedimine6hydroxybenzofuran derivatives were chemically synthesized and biologically evaluated as antibacterial and antifungal agents against candida albicans, escherichia coli, staphylococcus aureus, methicillinresistant staphylococcus aureus and bacillus subtilis. We found that the substituted salicylaldehydes containing different functional groups i. Benzofuran definition and meaning collins english dictionary. It is well known that vitamin e having chroman skeleton have a. For example, psoralen is a benzofuran derivative that occurs in several plants. Some physiological properties of benzofuran and dibenzofuran. Predicted data is generated using the us environmental protection agencys episuite. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. Wyeth claimed a class of thienopyrrole derivatives, such as 68, as potent 5ht 6 ligands cole, 2005.
In addition, benzofuran chalcone derivatives are foremost class of organic. Synthesis of optically enriched spirocyclic benzofuran. 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. Wo1999058527a2 benzofuran derivatives, pharmaceutical.
Suggested production of a guaiacyl benzofuran derivative from. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Solidstate emission enhancement via molecular engineering. It is the parent of many related compounds with more complex structures. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. The docking score with 1rjb is maximum with bh3oh and minimum with ba3,4,5och3. Synthesis of benzofuran pyrimidine derivatives 4ad, 5ad and 6ad. The invention refers to novel benzofuran derivatives of formula i, a process for preparing these compounds and to pharmaceutical compositions containing these active substances.
The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Benzofuran derivatives have wide range of biological activities as antioxidant, antiinflammatory and anticonvulsant agent. It may also be formed during other uses of coal or oil. Benzofurans and benzothiophenes 64 and 65 have been reported to be potent 5ht 6 ligands, comparable to their corresponding indole derivatives ahmed, 2005a. Novel benzofuran derivative dk1014 attenuates lung inflammation. In addition substituted benzofurans find application such. A diversity of synthetic routes can be applied to the synthesis of benzofurans.
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