Green synthesis and antioxidant activity of novel series of benzofurans from euparin extracted of Petasites hybridus

References

• Ackermann L, Kaspar LT. 2007. TiCl4-catalyzed indirect anti-Markovnikov hydration of alkynes: application to the synthesis of benzo [b] furans. J Org Chem. 72:6149–6153.10.1021/jo070887i
   PubMed Web of Science ®Google Scholar
• Alcaide B, Almendros P, Aragoncillo C. 2010. Highly reactive 4-membered ring nitrogen-containing heterocycles: synthesis and properties. Curr Opin Drug Disc Devel. 13:685–697.
   PubMedGoogle Scholar
• Anderson KW, Ikawa T, Tundel RE, Buchwald SL. 2006. The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans. J Am Chem Soc. 128:10964–10965.
   Web of Science ®Google Scholar
• Asseid FM, Duke CVA, Miller JM. 1990. A19F magic angle spinning nuclear magneti resonance and infrared analysis of the adsorption of alkali metal fluorides onto montmorillonite clay. Can J Chem. 68:1420–1424.10.1139/v90-217
   Web of Science ®Google Scholar
• Bandgar BP, Patil SA, Korbad BL, Biradar SC, Nile SN, Khobragade CN. 2010. Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents. Eur J Med Chem. 45(7):3223–3227.
   Google Scholar
• Bernini R, Cacchi S, De Salve I, Fabrizi G. 2007. Palladium-catalyzed synthesis of lipophilic benzo [b] furans from cardanol. Synthesis. 6:873–882.
   Google Scholar
• Cho CH, Neuenswander B, Lushington GH, Larock RC. 2008. Parallel synthesis of a multi- substituted benzo [b] furan library. J Comb Chem. 10:941–947.10.1021/cc800120y
   PubMedGoogle Scholar
• Dastoorani P, Maghsoodlou MT, Khalilzadeh MA, García-Granda S, Torre-Fernández L, Sarina E. 2016. Diastereoselective synthesis of novel benzofuran derivatives by euparin as a natural compound with DMAD in the presence of trialkyl phosphite. Heteroatom Chem. 27(2):102–107.10.1002/hc.21306
   Web of Science ®Google Scholar
• Dastoorani P, Maghsoodlou MT, Khalilzadeh MA, Sarina E. 2016. Synthesis of new dibenzofuran derivatives via Diels-Alder reaction of euparin with activated acetylenic esters. Tetrahedron Lett. 57:314–316.10.1016/j.tetlet.2015.12.021
   Web of Science ®Google Scholar
• De Luca L, Nieddu G, Porcheddu A, Giacomelli G. 2009. Some recent approaches to the synthesis of 2-substituted benzofurans. Curr Med Chem. 16:1–20.10.2174/092986709787002826
   PubMed Web of Science ®Google Scholar
• Dömling A. 2006. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev. 106:17–89.10.1021/cr0505728
   PubMed Web of Science ®Google Scholar
• Dondoni A. 2010. Heterocycles in organic synthesis: thiazoles and triazoles as exemplar cases of synthetic auxiliaries. Org Biomol Chem. 8:3366–3385.10.1039/c002586 k
   PubMed Web of Science ®Google Scholar
• Flynn BL, Hamel E, Jung MK. 2002. One-pot synthesis of benzo [b] furan and indole inhibitors of tubulin polymerization. J Med Chem. 45:2670–2673.10.1021/jm020077t
   PubMed Web of Science ®Google Scholar
• Gabriele B, Mancuso R, Salerno G, Costa M. 2007. Cascade reactions: a new synthesis of 2-benzofuran-2-ylacetamides by sequential Pd(0)-catalyzed deallylation-Pd(II)-catalyzed aminocarbonylative heterocyclization of 1-(2-allyloxyaryl)-2-yn-1-ols. J Org Chem. 72:9278–9282.10.1021/jo701956 k
   PubMed Web of Science ®Google Scholar
• Ganem B. 2009. Strategies for innovation in multicomponent reaction design. Acc Chem Res. 42:372–463.
   Web of Science ®Google Scholar
• Hajishaabanha F, Shaabani S, Shaabani A. 2016. Synthesis of furan-fused quinoxaline tetracyclic scaffolds via a three-component isocyanide-based reaction. Res Chem Intermed. 42:4109–4120.10.1007/s11164-015-2262-4
   Web of Science ®Google Scholar
• Hosseini-Sarvari M, Tavakolian M. 2012. Preparation, characterization, and catalysis application of nano-rods zinc oxide in the synthesis of 3-indolyl-3-hydroxy oxindoles in water. Appl Catal A. 441–442:65–71.10.1016/j.apcata.2012.07.009
   Web of Science ®Google Scholar
• Hosseini-Sarvari M, Sharghi H, Etemad S. 2008. Nanocrystalline ZnO for knoevenagel condensation and reduction of C–C double bond in conjugated alkenes. Helv Chim Acta. 91:715–724.10.1002/(ISSN)1522-2675
   Web of Science ®Google Scholar
• Hu P, Long M. 2016. Cobalt-catalyzed sulfate radical-based advanced oxidation: a review on heterogeneous catalysts and applications. Appl Catal B: Environ. 181:103–117.10.1016/j.apcatb.2015.07.024
   Web of Science ®Google Scholar
• Ismabery N, Lavila R. 2008. Heterocycles as key substrates in multicomponent reactions: the fast lane towards molecular complexity. Chem Eur J. 14:8444–8454.
   PubMed Web of Science ®Google Scholar
• Jacobsen M, Crosby DG. 1971. Natural occuring insecticides. New York (NY): Dekker.
   Google Scholar
• Khaleghi F, Bin Din L, Jantan I, Yaacob WA, Khalilzadeh MA. 2011. A facile synthesis of novel 1,4-benzoxazepin-2-one derivatives. Tetrahedron Lett. 52:7182–7184.10.1016/j.tetlet.2011.10.129
   Web of Science ®Google Scholar
• Khaleghi F, Bin Din L, Rostami Charati F, Yaacob WA, Khalilzadeh MA, Skelton B, Makha M. 2011. A new bioactive compound from the roots of Petasites hybridus. Phytochem Lett. 4: 254–258.10.1016/j.phytol.2011.04.009
   Web of Science ®Google Scholar
• Khaleghi F, Jantan I, Bin Din L, Yaacob Wan A, Khalilzadeh MA, Abbas Bukhari SN. 2014. Immunomodulatory effects of 1-(6-hydroxy-2- isopropenyl-1-benzofuran-5-yl)-1-ethanone from Petasites hybridus and its synthesized benzoxazepine derivatives. J Nat Med. 68:351–357.10.1007/s11418-013-0805-9
   PubMed Web of Science ®Google Scholar
• Kouzu M, Kasuno T, Tajika M, Sugimoto Y, Yamanaka S, Hidaka J. 2008. Calcium oxide as a solid base catalyst for transesterification of soybean oil and its application to biodiesel production. Fuel. 87:2798–2806.10.1016/j.fuel.2007.10.019
   Web of Science ®Google Scholar
• Murata M, Yasumoto T. 2000. The structure elucidation and biological activities of high molecular weight algal toxins: maitotoxin, prymnesins and zooxanthellatoxins. Nat Prod Rep. 17:293–314.10.1039/a901979 k
   PubMed Web of Science ®Google Scholar
• Nagamochi M, Fang YQ, Lautens M. 2007. A general and practical method of alkynyl indole and benzofuran synthesis via tandem Cu- and Pd-catalyzed cross-couplings. Org Lett. 9:2955–2958.10.1021/ol071370w
   PubMed Web of Science ®Google Scholar
• Nevagi RJ, Dighe SN, Dighe SN. 2015. Biological and medicinal significance of benzofuran. Eur J Med Chem. 97:561–581.10.1016/j.ejmech.2014.10.085
   PubMed Web of Science ®Google Scholar
• Radhakrishan R, Do DM, Jaenicke S, Sasson Y, Chuah GK. 2011. Potassium phosphate as a solid base catalyst for the catalytic transfer hydrogenation of aldehydes and ketones. ACS Catal. 1:1631–1636.10.1021/cs200299v
   Web of Science ®Google Scholar
• Rateb NM, Elnagdy SM, Zohdi HF. 2014. Neural responses to functional and experiential ad appeals: explaining ad effectiveness. Int J Adv Res. 2:355–366.
   Google Scholar
• Rentzea C, Reissenwebe G, Feuerherd KH, Jung J. 1983. An expedient synthesis of enantioenriched substituted benzofuran. Ger Pat Offen. 3:139250.
   Google Scholar
• Rostami-Charati F, Hossaini Z, Khalilzadeh M. 2012. Novel isocyanide-based three-component synthesis of substituted 9Hfuro[2,3-f]chromene-8,9- dicarboxylates in water. Comb Chem High T Scr. 15:433–437.
   PubMed Web of Science ®Google Scholar
• Ruijter E, Scheffelaar R, Orru RVA. 2011. Multicomponent reaction design in the quest for molecular diversity & complexity. Angew Chem Int Ed. 50:6324–6346.
   PubMed Web of Science ®Google Scholar
• Sabbaghan M, Anaraki Firooz A, Jan Ahmadi V. 2012. The effect of template on morphology, optical and photocatalytic properties of ZnO nanostructures. J Mol Liq. 175:135–140.10.1016/j.molliq.2012.08.019
   Web of Science ®Google Scholar
• Sajjadi-Ghotbabadi H, Javanshir S, Rostami-Charati F. 2017. Synthesis, characterization, and antioxidant evaluations of new 2-oxochromene and benzofuran derivatives catalyzed by KF/CP. J Heterocyclic Chem. 54:979–985.10.1002/jhet.v54.2
   Web of Science ®Google Scholar
• Sakamoto T, Kondo Y, Yasuhara A, Yamanaka H. 1991. Condensed heteroaromatic ring systems. XVIII. Palladium-catalyzed cross-coupling reaction of aryl bromides with (Z)-1-ethoxy-2-tributylstannylethene and its utilization for construction of condensed heteroaromatics. Tetrahedron. 47:1877–1886.10.1016/S0040-4020(01)96100-9
   Web of Science ®Google Scholar
• Saku O, Saki M, Kurokawa M, Ikeda K, Uchida SI, Takizawa T, Uesaka N. 2010. Synthesis studies on selective adenosine A2A receptor antagonists. Part II: synthesis and structure-activity relationships of novel benzofuran derivatives. Bioorg Med Chem Lett. 20:3768–3771.10.1016/j.bmcl.2010.04.058
   PubMed Web of Science ®Google Scholar
• Sasaki N, Kudo S, Endo K, Suzuki R. 1992. Chem Abstr. 117:178993v.
   Google Scholar
• Saundane AR, Nandibeoor MK. 2015. Synthesis, characterization, and biological evaluation of Schiff bases containing indole moiety and their derivatives. Monatsh Chem. 146:1751–1761.10.1007/s00706-015-1440-9
   Web of Science ®Google Scholar
• Shaterian HR, Mohammadnia M. 2013. Effective preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene and hydroxyl naphthalene-1,4-dione derivatives under ambient and solvent-free conditions. J Mol Liq. 177:353–360.10.1016/j.molliq.2012.10.012
   Web of Science ®Google Scholar
• Teimouri MB, Khavasi HR. 2007. One-pot three-component regioselective synthesis of linear naphtho[2,3-b]-furan-4,9-diones. Tetrahedron. 63:10269–10275.10.1016/j.tet.2007.07.082
   Web of Science ®Google Scholar
• Telvekar VN, Belubbi A, Bairwa VK, Satardekar K. 2012. Novel N′-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents. Bioorg Med Chem Lett. 22:2343–2346.10.1016/j.bmcl.2012.01.067
   PubMed Web of Science ®Google Scholar
• Varma RS. 1999. Solvent-free organic syntheses using supported reagents and microwav irradiation. Green Chem. 1:43.10.1039/a808223e
   Web of Science ®Google Scholar
• Watanabe M, Yamamoto T, Nishiyama MA. 2000. A new palladium-catalyzed intramolecular cyclization: synthesis of 1-aminoindole derivatives and functionalization of their carbocylic rings. Angew Chem Int Ed. 39:2501–2504.10.1002/(ISSN)1521-3773
   PubMed Web of Science ®Google Scholar
• Whitby LR, Lee AM, Kunz S, Oldstone MBA, Boger DL. 2009. Characterization of lassa virus cell entry inhibitors: determination of the active enantiomer by asymmetric synthesis. Bio org Med Chem Lett. 19:3771–3774.10.1016/j.bmcl.2009.04.098
   PubMed Web of Science ®Google Scholar
• Willis MC, Taylor D, Gillmore AT. 2004. Palladium-catalyzed intramolecular o- arylation of enolates: application to benzo [b] furan synthesis. Org Lett. 6:4755–4757.10.1021/ol047993 g
   PubMed Web of Science ®Google Scholar
• Xie YS, Kumar D, Bodduri VDV, Tarani PS, Zhao BX, Miao JY, Jang K, Shin DS. 2014. Microwave-assist parallel synthesis of benzofuran-2-carboxaide derivatives bearing anti-infiammatory, analgesic and antipyretic agents. Tetrahedron Lett. 55:2796–2800.10.1016/j.tetlet.2014.02.116
   Web of Science ®Google Scholar
• Yamashita A, Toy A, Scahill T. 1989. Synthesis of khellin and its analogs via chromium carbene complexes. J Org Chem. 54:3625–3634.10.1021/jo00276a024
   Web of Science ®Google Scholar
• Yu ZY, Brannigan JA, Moss DK, Brzozowski AM, Wilkinson AJ, Holder AA, Tate EW, Leatherbarrow RJ. 2012. Design and synthesis of inhibitors of Plasmodium falciparum N-myristoyltransferase, a promising target for antimalarial drug discovery. J Med Chem. 55:8879–8890.10.1021/jm301160 h
   PubMed Web of Science ®Google Scholar
• Zhu J, Bienayme H. 2005. Multicomponent reactions, Wiley-VCH, Weinheim.
   Google Scholar