Synthesis of optically enriched spirocyclic benzofuran. The derivatives of keto benzofuran are useful as medicines, such as amiodarone and benziodarone, particulary for. Pdf synthesis of some benzofuran derivatives containing. 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. Synthesis and biological evaluation of new benzofuran. Jul 18, 2006 benzofuran derivatives, process for the preparation of the same and uses thereof. The production mechanism and a parallel occurring reaction were also demonstrated. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. School of dentistry at niigata, the nippon dental university, hamaura. Usually these are called as benzofuran and isobenzofuran respectively figure 1. In addition substituted benzofurans find application such. 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. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose.
The docking score with 1rjb is maximum with bh3oh and minimum with ba3,4,5och3. Benzofuran definition and meaning collins english dictionary. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin. Wo1999058527a2 benzofuran derivatives, pharmaceutical. Novel benzofuran derivatives bearing naryl piperazine moiety. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open.
It is the parent of many related compounds with more complex structures. Benzofuran derivatives, process for the preparation of the same and uses thereof. 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. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad. The key benzofuran analog 66 bvt74316 was recently reported to be in phase i development. Benzofuran derivatives are often applied to medical use, antiseptic, pesticide, fuel additive and so on. Suggested production of a guaiacyl benzofuran derivative from. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. 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. Journal of chemical and pharmaceutical research, 2017, 95. Antitubercular activity of benzofuran and naphthofuran derivatives.
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. A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes. 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. 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. Synthesis and antimicrobial evaluation of 3substituted. Pdf in this investigation, the synthesis of 2substituted pyrimidines by the reaction of benzofuran. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Wyeth claimed a class of thienopyrrole derivatives, such as 68, as potent 5ht 6 ligands cole, 2005. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials.
Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. The part of the coal oil that contains 2,3 benzofuran is made into a plastic called coumaroneindene resin. Benzofuran article about benzofuran by the free dictionary. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. In addition, benzofuran chalcone derivatives are foremost class of organic. Benzofuran synthesis through iodocyclization reactions. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. In addition substituted benzofurans find application such as of fluorescent sensor 17, oxidant 18, antioxidants, brightening agents, a variety of drugs and in. The structure of this compound was determined as benzofuran derivative. Journal of chemical and pharmaceutical research, 2012, 4. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. It is well known that vitamin e having chroman skeleton have a. Furthermore, scientists at roche have demonstrated that the pyrazolotriazine 69 template was a good replacement for indole in terms of 5ht 6.
For example, psoralen is a benzofuran derivative that occurs in several plants. We found that the substituted salicylaldehydes containing different functional groups i. Synthesis of polyfunctionalized benzofurans via onepot domino. The docking score with 3fdn is maximum with bh3oh and minimum with ba4ch3. 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. Benzofurans heterocyclic building blocks sigmaaldrich. Benzofuran definition of benzofuran by the free dictionary. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. 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. Benzofuran is maillard produced present in roasted coffee aroma. Benzofuran is the parent of many related compounds with more complex structures. The structures of all the newly synthesized compounds have been established by spectral studies. Benzofuran and its derivatives have attracted medicinal chemists and pharmacologists due to their pronounced biological activities and their potential applications.
Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Synthesis of chalcone derivatives of benzo furan as. It may also be formed during other uses of coal or oil. Rather, the part of the coal oil that contains 2,3 benzofuran is made into a plastic called coumaroneindene resin. Benzofurans are chemical compounds which contain a benzofuran ring in their structure. This study reports that a novel phenolic benzofuran derivative could be obtained selectively from g1 by further alkaline treatment. Derivatives from tyrosol simple and efficient synthesis of. The simple benzofuran derivatives like 2nitrobenzofuran 2, 2acetyl benzofurans are well known as biodynamic agents possessing various pharmacological properties i. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Synthesis of 2,3difunctionalized benzofuran derivatives through. An efficient synthesis of benzofuran derivatives under. An international journal for rapid communication of synthetic organic chemistry, 44.
Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Benzofuran as a promising scaffold for the synthesis of. Benzofuran derivatives galileo pharmaceuticals, inc. Solidstate emission enhancement via molecular engineering. Suggested production of a guaiacyl benzofuran derivative. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl.
Onepot synthesis of novel symmetric 1,5dibenzofuran2. Benzofuran derivatives have wide range of biological activities as antioxidant, antiinflammatory and anticonvulsant agent. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. Herein, the series of benzofuran derivatives have been prepared by applying the methods mentioned above. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. 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. Benzofurane derivatives, preparation method, use as medicines and pharmaceutical compositions containing same. 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. Predicted data is generated using the us environmental protection agencys episuite.
Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. 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. Benzofuran derivatives display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor, activities. 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. Synthesis of new benzofuran2carboxylic acid derivatives. Though there are many methodology are available for designing and developing newer drug. Some physiological properties of benzofuran and dibenzofuran. Moreover, 7piperazinylbenzofuran2carbxylic acid amides having halogens or methoxyl groups in benzene ring were patented as partial agonists of 5ht receptors which should. Synthesis of benzofuran pyrimidine derivatives 4ad, 5ad and 6ad. Most compounds showed a selective antibacterial activity to grampositive bacteria and four. 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. Onepot synthesis protocol for highly functionalized benzofuran scaffold preetpal s sidhu department of chemistry and biochemistry university of wisconsin, milwaukee, wi email. A number of optically enriched spirocyclic benzofuran.
A series of novel hybrid compounds between benzofuran and naryl piperazine have been synthesized. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. Design, synthesis, and biological evaluation of novel benzofuran. Synthesis of 2, 3difunctionalized benzofuran derivatives through. The part of the coal oil that contains 2,3benzofuran is made into a plastic called coumaroneindene resin. Synthesis of some benzofuran derivatives containing pyrimidine. 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. These are only a few examples from a large group of benzofurans with anticancer activity.
Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. Benzofuran derivatives have drawn considerable attention due to their. A diversity of synthetic routes can be applied to the synthesis of benzofurans. Michael addition reaction of substituted benzofuran. Under no circumstances may this pdf file be placed on a network of any sort without our express permission. Benzofurans and benzothiophenes 64 and 65 have been reported to be potent 5ht 6 ligands, comparable to their corresponding indole derivatives ahmed, 2005a.
Jan 02, 1990 2,3 benzofuran is a colorless, sweetsmelling, oily liquid which does not mix with water. 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. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. The successful use of various iodinating agents, bases, additives etc. Benzofuran derivatives are valuable structural motifs that are often found. All the ligands were prepared for molecular docking by merging the nonpolar. The outstanding development of benzofuran derivatives in diverse diseases in very short span of time proves its magnitude for medicinal chemistry research. Novel benzofuran derivative dk1014 attenuates lung inflammation. Synthesis of new derivatives of benzofuran as potential. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. 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 docking score of benzofuran derivatives of ba series is ranging from 3.
350 323 278 998 340 367 1072 1384 760 946 1280 834 300 382 10 131 376 751 862 1243 1389 469 1401 1338 986 727 1066 487 1233 1027 471 786 1248 1265 998 805 258 1017 159 1435 1204 496 925