A series of benzofuran derivatives were designed and synthesized, and their inhibitory activites were measured against the sirt. Through a sequence involving an interrupted pummerer reaction and 3,3 sigmatropic rearrangement, phenols can be combined with readily accessible yet synthetically unexplored benzothiophene soxides to provide c3arylated benzofuran products. Suggested production of a guaiacyl benzofuran derivative. Han department of endocrinology, royal free and university college medical school, royal free hospital, hampstead, london nw3 2qg, uk, and. The free radical scavenging potentialities of the compounds 7 were. 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. Several isoxazole derivatives are found to possess antitubercular, antimicrobial and antiinflammatory activities. Pdf a facile electrochemical method for synthesis of new. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. Herein, we present a short and highly modular synthetic route that involves 8aminoquinoline directed ch arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran2carboxamides. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. 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. One of the best methods for an access to benzofuran derivatives is sonogashira crosscoupling reaction between ohalo phenol and terminal alkynes followed by sequential 5endodig cyclization.
Here we report a general and practical protocol for regioselective dearomative annulation of indole and benzofuran derivatives in an electrochemical way. An international journal for rapid communication of synthetic organic chemistry, 44. Discovery of benzofuran derivatives that collaborate with insulin. We have discussed here significant biological properties of these derivatives such as antitumor, antimicrobial, antihyperglycemic, analgesic, antiinflammatory, antiviral, antipyretic activities etc. Bioactive benzofuran derivatives from cortex mori radicis, and their neuroprotective and analgesic activities mediated by mglur 1 by yanan wang 1, maofeng liu 1, weizhen hou 1, ruiming xu 1, jie gao 2, anqi lu 1, meiping xie 1, lan li 1, jianjun zhang 1, ying peng 1, lili ma 3, xiaoliang wang 1, jiangong shi 1 and sujuan. Pdf synthesis of new derivatives of benzofuran as potential. This dissertation is brought to you for free and open access by the iowa state university capstones, theses and dissertations at iowa state university. Synthesis of 3benzofuranyl2oxindole and 3spirooxindole benzofuran derivatives. Benzofuran derivatives and their antitubercular, anti. Thus, benzofuran derivatives play an important role in inhibiting telomerase enzyme. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. Some physiological properties of benzofuran and dibenzofuran derivatives. Dec 10, 20 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. It is well known that vitamin e having chroman skeleton have a.
For the directed ch arylation reactions, pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the c3 position of the benzofuran. Transitionmetal free cyclization of propargylic alcohols with aryne. Pnre comljounds either as the free phenols, the methyl ether, or the methyl etheracetate derivatives were isolated by a variety of. Through this strategy, at least one free hydroxyl group was introduced into the benzene ring in a substitution. In the present study, we synthesized a series of novel 7methoxynsubstituted phenylbenzofuran2carboxamide derivatives in moderate to good yields and evaluated their neuroprotective and antioxidant activities using primary cultured rat cortical neuronal cells and in vitro cell free bioassays. Electrooxidation enables highly regioselective dearomative. Harmalkar, xuezhen xu, kyusic jang, kyeong lee bk21plus rfind team, college of pharmacy, dongguk universityseoul, goyang 410820, republic of korea a r t i c l e i n f o a b s t r a c t. Transitionmetal free cyclization of propargylic alcohols. Us8318800b2 solid pharmaceutical compositions containing. Benzofuran derivatives from alkynylsubstituted benzynes and. A complex benzofuran derivative is constructed by a unique free radical cyclization cascade, which is an excellent method for the synthesis of a series of difficultto. Benzofuran definition of benzofuran by the free dictionary.
Yuhang miao abcd, yuheng hu abcd, jie yang abcd, teng liu abcd, jie sun abcd and xiaojing wang abcd a school of medicine and life sciences, university of jinan, shandong academy of medical sciences, jinan 250200, shandong, china. Given the vast number of applications of benzofuranbased drugs in todays medicine, there exists considerable interest for novel synthetic methodologies that can grant expedient access to new kinds of. Benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer. A series of novel hybrid compounds between benzofuran and naryl piperazine. Synthesis and hplc method validation of novel 3fluoron7methoxy24methoxyphenyl1benzofuran5ylmethylaniline on free shipping on qualified orders. The protocol offers a transitionmetal free and operationally simple methodology with broad substrate scope as a ready access to complex oxindolelinked heterocyclic compounds. For example, psoralen is a benzofuran derivative that occurs in several plants. Request pdf benzofuran derivatives and the thyroid amiodarone and dronedarone are two clinically important benzofuran derivatives. Synthesis of elaborate benzofuran2carboxamide derivatives. The benzofuran nucleus and derivatives occupy apposition of considerable significance for widespread occurrence in plants and their. Moracins aez in medicinal chemistry ravi naik, dipesh s. This chloroacetylbenzofuran on treatment with urea in ethanol gives 4 1benzofuran2yl 1, 3oxazole2amine. The results of our previous research indicated that some derivatives of benzofurans, particularly halogenoderivatives, are selectively toxic towards human.
It has been found that a group of rubromycins and their analogs, a class of quinone antibiotics that possess a benzofuran system, strongly inhibit human telomerase enzyme, which leads to telomere shortening, arrest of cell growth and apoptosis 25. The supporting information is available free of charge on the acs. Benzofuran derivatives as tubulin polymerization inhibitors ref. Read benzofuran derivatives from ligularia stenocephala, journal of the chinese chemical society on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Transitionmetalfree synthesis of c3arylated benzofurans. Synthesis, antimicrobial, and antioxidant activity of. Benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc. Compared with conventional heating, this microwave.
A series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were synthesized as potential antitumor agents. Sep 21, 2016 benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. The characterization of synthesized compounds was identified on the basis of ir, nmr, mass and elementary analysis.
Neuroprotective and antioxidant effects of novel benzofuran2. Benzofuran derivatives from alkynylsubstituted benzynes. Novel 18flabeled benzofuran derivatives with improved properties for positron emission tomography pet imaging of. Synthesis and biological activities of some benzofuran. Expired lifetime application number us293564a inventor jurd leonard original assignee. If the benzofuran fraction is largely free from indene, benzofuran can be concentrated further through either selective extraction or azeotropic distillation with alkylene glycols. Journal of chemical and pharmaceutical research, 2017, 95. Another benzofuran ring constructed by proton quantum tunneling has not. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. New benzofuran derivatives as an antioxidant agent. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Natural and synthetic benzofuran derivatives are a class of important. Pdf natural source, bioactivity and synthesis of benzofuran. A ligandfree cubrcatalyzed couplingcyclization of terminal alkynes 83 with.
The antiinflammatory activity of the benzofuran derivatives 1 was. Amiodarone has been used widely for treating resistant tachyarrhythmias in the past three decades. Smith, earl westley, some physiological properties of benzofuran and dibenzofuran derivatives 1936. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Benzofuran derivatives possess a broad spectrum of chemotherapeutic properties, and some of benzofuran based compounds have already used in clinics for the treatment of various diseases, so benzofuran derivatives occupy an important position in the development of new drugs. Exploring the multitarget neuroprotective chemical space. A series of substituted benzofuran derivatives were synthesized and characterized by spectral data. Preparation of a biologically active benzofuran derivative ethyl. Natural source, bioactivity and synthesis of benzofuran derivatives yuhang miao, abcd yuheng hu,abcd jie yang,abcd teng liu,abcd jie sun abcd and xiaojing wangabcd benzofuran compounds are a class of compounds thatare ubiquitous in nature. It is recovered either by precipitation as the dibromide or the picrate, or by sulfonation in acetic anhydride, followed by decomposition of the benzofuran derivatives. H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran 2carboxamides. Agatsuma t, furukawa h, hayakawa i, shioya r, sugano y 2004 thienopyridine and benzofuran derivatives as potent antitumor agents possessing different structureactivity relationships. The benzofuran derivatives were obtained by the reaction of various salicylaldehydes in acetone, and then hydrolyzed to the corresponding carboxylic acids. Amiodarone and dronedarone are two clinically important benzofuran derivatives.
Molecules free fulltext bioactive benzofuran derivatives. Read synthesis of benzofuran derivatives as selective inhibitors of tissuenonspecific alkaline phosphatase. Pdf reactivity of benzofuran derivatives researchgate. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. Benzofuran derivatives display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor, activities. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Synthesis of 3benzofuranyl2oxindole and 3spirooxindole benzofuran derivatives organic letters.
Abstractsix nglycosyl benzofuran derivatives were synthesized by the catalysis of organic bases and condensation agents. Synthesis and studying of antimicrobial and antioxidant. The structures of all compounds were established on the basis of analytical and spectral data. Benzofuran derivatives as cytotoxic and inhibitors of mtor signalling agents ref.
A facile electrochemical method for synthesis of new benzofuran derivatives. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. Natural source, bioactivity and synthesis of benzofuran. These products were synthesized starting with 2bromoacetylbenzofuran 1. Synthesis of potent antitumor and antiviral benzofuran. Substituted benzofurans also posses other applications such as fluorescent sensor, antioxidants, oxidant, brightening agents and in other field of chemistry and agriculture. Natural source, bioactivity and synthesis of benzofuran derivatives. A series of benzofuran derivatives have been synthesized by use of a microwaveassisted process. 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 corresponding compound on treatment with various aldehydes to give different derivative. A complex benzofuran derivative is constructed by a unique free radical cyclization cascade, which is an excellent method for the synthesis of a series of di. Synthesis of benzofuran derivatives via different methods. The invention relates to a process for the preparation of 3benzoyl benzofuran derivatives of general formula.
Some of the synthesized compounds were tested for in vitro. Benzofuran derivatives from ligularia stenocephala. Methicillin and vancomycinresistant staphylococcus aureus strains are responsible for most infections of this type 90,91. Transitionmetalfree cyclization of propargylic alcohols. This investigation is essential to find the chemical. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. With this method, a large number of hydroxylated benzofuran derivatives with different substitution. An insight on lead developments, radioligands and advances of the last decade. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Us5266711a process for the preparation of 3benzoyl.
A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes. Us3165537a us293564a us29356463a us3165537a us 3165537 a us3165537 a us 3165537a us 293564 a us293564 a us 293564a us 29356463 a us29356463 a us 29356463a us 3165537 a us3165537 a us 3165537a authority us united states prior art keywords ml benzofuran methanol product formula vi prior art date 19630708 legal status the legal status is an assumption and is not. Molecular docking on free shipping on qualified orders. Synthesis and ache inhibitory activity of nglycosyl. A series of benzofuran derivatives with neuroprotective activity in collaboration with. Furthermore, other benzofuran derivatives have been shown to display a wide range of antimicrobial and anticancer properties 1,2,3,4,5,6,7. Amiodarone has been used widely for treating resistant. Bioactive benzofuran derivatives from cortex mori radicis, and their neuroprotective and analgesic activities mediated by mglur 1. Synthesis and evaluation of novel benzofuran derivatives. Dec 10, 2012 buy hplc method validation benzofuran derivatives. Jan 29, 2016 buy computational study of 1benzofuran derivatives.
Furthermore, the 2methylbenzofuran derivatives 9 were synthesized using. The structure of this compound was determined as benzofuran derivative. The characterization of synthesized compounds was identified on the basis of. Benzofuran as a promising scaffold for the synthesis of. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Sonogashira reaction has been performed usually in the presence of pdii catalyst together with copper or under copper free condition.
We report a transitionmetal free synthesis of benzofurans from benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Design, synthesis, and biological evaluation of novel benzofuran. Benzofuran derivatives and the thyroid request pdf. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Pdf aryl benzofuran derivatives from the stem bark of. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents.
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 a series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to. The present invention relates to a solid pharmaceutical composition for oral administration characterized in that it comprises a benzofuran derivative with antiarrhythmic activity, or one of the pharmaceutically acceptable salts thereof, as an active principle, and a pharmaceutically acceptable nonionic hydrophilic surfactant optionally in combination with one or more pharmaceutical excipients. Guaiacyl benzofuran from sw, bioresources 1, 69326939. Novel 18flabeled benzofuran derivatives with improved. Methicillin and vancomycinresistant staphylococcus aureus strains are responsible for. Benzofuran is the parent of many related compounds with more complex structures. H arylation reactions, pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the c3 position of the. A complex benzofuran derivative is constructed by a unique free radical cyclization. This chloroacetylbenzofuran on treatment with urea in ethanol gives 4 1 benzofuran 2yl 1, 3oxazole2amine. Proof of their strucune was based mainly on 2dnmr as well as highresolution ms and cd experiments. Benzofurans and benzothiophenes 64 and 65 have been reported to be potent 5ht 6 ligands, comparable to their corresponding indole derivatives ahmed, 2005a.
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