Login Register Cart 0
Generic placeholder image

Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Benzofuran: A Key Heterocycle - Ring Closure And Beyond

Author(s): Andiappan Lavanya, Kilambi Narasimhan* and Vediappen Padmini

Volume 17, Issue 3, 2020

Page: [224 - 276] Pages: 53

DOI: 10.2174/1570193X16666190710122912

Price: $65

Abstract

The benzofuranyl motif present in compounds exhibits various medicinal properties and non-drug applications. These derivatives are naturally occurring compounds or synthetic materials, which cover a broad spectrum of pharmacological activities like anti-inflammatory, anti-diabetic, anti- depressant, anti-HIV, anti-microbial, anti-proliferative, anti-convulsant, cytotoxic, analgesic, etc. Few of the commercially interesting compounds from this class are, ailanthoidol (anti-inflammatory), amiodarone, dronedarone, celivarone (anti-arrhythmic), bufuralol (muscular airways relaxant), morphine, 5-(2-aminopropyl)benzofuran; 5-APB, 6-(2-aminopropyl)benzofuran; 6-APB (CNS), rifampicin (antibiotic), etc., whereas, some of the non-drug applications are in perfumery industry (bergapten) and as tannin activators in sunscreen preparations (psoralen, 8-methoxypsoralen, and angelicin). Considering these interesting biological activities and commercial utilities, a review on the synthetic aspects of this privileged scaffold was attempted. For the benefit of natural product-based drug discovery, available sources of these derivatives, extraction process and reported biological activities have also been outlined in this review.

Keywords: Benzofuran derivatives, drug and non-drug application, metal catalysts, ring-closure, cytotoxicity, syntheticstrategies.

« Previous Next »
Graphical Abstract

[1]
Brenda, M.; René, T.; Michelle, D.S.P.; Katherine, S.; Adriana, A.; Raúl, C.; Pablo, C. In vitro antiproliferative activity of 3 H-spiro [1-benzofuran-2,1′-cyclohexane] derivatives. Bol. Latinoam. Caribe Plantas Med. Aromat., 2011, 3, 281-288.
[2]
Bakr, F.; Wahab, A.; Aziz, H.A.A; Ahmed, S.M. Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl]-1H-pyrazoles. Eur. J. Med. Chem., 2009, 44, 2632-2635.
[http://dx.doi.org/10.1016/j.ejmech.2008.09.029] [PMID: 18995932]
[3]
Jerzy, K; Mariol, K; Bożena, K; Joann, S; Iren, W Synthesis and preliminary evaluation of the antimicrobial activity of selected 3-benzofurancarboxylic acid derivatives. Molecules, 2010, 15, 4737-4749.
[http://dx.doi.org/10.3390/molecules15074737] [PMID: 20657389]
[4]
Vrushali, P.; Ashish, A.; Shantanu, P.; Bobade, A.S.; Chowdhary, A.S. Synthesis of 5-aryl-3-(5-bromo-3-benzofuran-2-yl)-1-pyrazole as antimicrobial agent. IOSR J. Phar. Biol. Sci., 2013, 8, 4-8.
[5]
Sangeetha, M.; Brijendra, K.S.; Tribhuvan, S.; Chetan, M.B.; Mudshinge, S.R. In-vitro anti-inflammatory studies of 3-(1-Benzofuran-2-yl)-5-(substituted aryl) isoxazole. Int. J. Res. Pharm. Biomed. Sci., 2011, 2, 1203-1205.
[6]
Dauzonne, D.; Gillardin, J.M.; Lepage, F.; Pointetl, R.; Lamottel, G.; Demersemanl, P. Synthesis and some CNS activities of new benzofuranylacryloylpiperazines. Eur. J. Med. Chem., 1995, 30, 53-59.
[http://dx.doi.org/10.1016/0223-5234(96)88209-2]
[7]
Rindhe, S.S.; Rode, M.A.; Karale, B.K. New benzofuran derivatives as an antioxidant agent. Indian J. Pharm. Sci., 2010, 72(2), 231-235.
[http://dx.doi.org/10.4103/0250-474X.65022] [PMID: 20838529]
[8]
Heidari, M.R.; Foroumadi, A.; Noroozi, H.; Samzadeh-Kermani, A.; Azimzadeh, B.S. Study of the anti-inflammatory and analgesic effects of novel rigid benzofuran-3, 4-dihydroxy chalcone by formalin, hot-plate and carrageenan tests in mice. Pak. J. Pharm. Sci., 2009, 22(4), 395-401.
[PMID: 19783518]
[9]
Patel, H.J.; Sarra, J.; Caruso, F.; Rossi, M.; Doshi, U.; Stephani, R.A. Synthesis and anticonvulsant activity of new N-1′,N-3′-disubstituted-2‘H,3H,5’H-spiro-(2-benzofuran-1,4′-imidazolidine)-2′,3,5′-triones. Bioorg. Med. Chem. Lett., 2006, 16(17), 4644-4647.
[http://dx.doi.org/10.1016/j.bmcl.2006.05.102] [PMID: 16793262]
[10]
Dimple, P.; Chandrashekar, J.; Pradeep, K.R. Synthesis and characterization of n 2 -substituted benzene sulfonyl n 1 - 5-substituted benzofuran-2-carbohydrazide for their anti-diabetic activity. World J. Phar. Pharm. Sci., 2014, 4, 1500-1508.
[11]
El-Zahar, M.I.; Abd El-Karim, S.S.; Haiba, M.E.; Khedr, M.A. Synthesis, antitumor activity and molecular docking study of novel benzofuran-2-yl pyrazole pyrimidine derivatives. Acta Pol. Pharm. Drug Res., , 2011, 68(3), 357-373.
[12]
Hranjec, M.; Sovic, I.; Ratkaj, I.; Pavlovic, G.; Ilic, N.; Valjalo, L.; Pavelic, K.; Pavelic, S.K.; Karminski-Zamola, G. Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: cell death mechanisms and determination of crystal structure. Eur. J. Med. Chem., 2013, 59, 111-119.
[http://dx.doi.org/10.1016/j.ejmech.2012.11.009] [PMID: 23220640]
[13]
Rida, S.M.; El-Hawash, S.A.; Fahmy, H.T.; Hazzaa, A.A.; El-Meligy, M.M. Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation of in vitro anti-HIV-1, anticancer and antimicrobial activities. Arch. Pharm. Res., 2006, 29(10), 826-833.
[http://dx.doi.org/10.1007/BF02973901] [PMID: 17121175]
[14]
Ravikumar, S.; Ramanathan, G.; Gnanadesigan, M Antagonistic properties of seagrass associated Streptomyces sp. RAUACT-1: A source for anthraquinone rich compound. Asian Pac. J. Trop. Med., 2012, 5, 358-361.
[http://dx.doi.org/10.1016/S1995-7645(12)60165-5] [PMID: 22546651]
[15]
Ramalakshmi, S.; Muthuchelian, K. Analysis of bio-active constituents of the ethanolic leaf extract of Tabebuia rosea (Bertol.) DC by gas chromatography-mass spectrometry. Int. J. Chemtech Res., 2011, 3, 1054-1059.
[16]
Yusof, H.; Din, L.B.; Yaacob, W.A. Benzofuran glycosides from styrax benzoin. Malaysian. J. Anal. Sci., 2014, 18, 676-682.
[17]
Dharmalingam, R.; Nazni, P. Phytochemical evaluation of Coriandrum L. flowers. Int. J. Food and Nutri. Sci., 2013, 2, 34-39.
[18]
Rajeswari, G.; Murugan, M.; Mohan, V.R. GC-MS analysis of bioactive components of Hugonia mystax L. (Linaceae). J. Pharm. Biomed. Sci., 2013, 29, 818-824.
[19]
Faramarz, R.C.; Seyed, A.R.; Mehdi, S.; Ahmad, M.; Mohammad, R.H.T. Microwave assisted extraction of benzofurane derivatives from Petasites hybridus rhizomes. Ira. J. Org. Chem., 2011, 3, 725-727.
[20]
Antara, S.; Amla, B.; Asian, J. Chemical composition of methanol extract of the leaves of Melia Azedarach L. Phar.l and Clin. Res., 2012, 5, 42-45.
[21]
Lear, M.J.; Simon, O.; Foley, T.L.; Burkart, M.D.; Baiga, T.J.; Noel, J.P.; DiPasquale, A.G.; Rheingold, A.L.; La Clair, J.J. Laetirobin from the parasitic growth of Laetiporus sulphureus on Robinia pseudoacacia. J. Nat. Prod., 2009, 72(11), 1980-1987.
[http://dx.doi.org/10.1021/np9002838] [PMID: 19842686]
[22]
Simonetti, S.O.; Larghi, E.L.; Bracca, A.B.J.; Kaufman, T.S. Angular tricyclic benzofurans and related natural products of fungal origin. Isolation, biological activity and synthesis. Nat. Prod. Rep., 2013, 30(7), 941-969.
[http://dx.doi.org/10.1039/c3np70014c] [PMID: 23719995]
[23]
Han, T.S.; Williams, G.R.; Vanderpump, M.P.J. Benzofuran derivatives and the thyroid. Clin. Endocrinol. (Oxf.), 2009, 70(1), 2-13.
[http://dx.doi.org/10.1111/j.1365-2265.2008.03350.x] [PMID: 18727707]
[24]
Khanam, H.; Shamsuzzaman, Bioactive Benzofuran derivatives: A review. Eur. J. Med. Chem., 2015, 97, 483-504.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.039] [PMID: 25482554]
[25]
Hiremathad, A.; Patil, M.R.C.K.R., K.; Chand, M.A.; Santos, ; and R.S., Keri Benzofuran: An emerging scaffold for antimicrobial agents. RSC Advances, 2015, 5, 96809-96828.
[http://dx.doi.org/10.1039/C5RA20658H]
[26]
Ashish, R.; Anamik, S. Bioactive Benzofuran derivatives: An insight on lead developments, radio ligands and advances of the last decade. Eur. J. Med. Chem., 2014, 97, 356-376.
[http://dx.doi.org/10.1016/j.ejmech.2015.01.021]
[27]
Khodarahmi, G.; Asadi, P.; Hassanzadeh, F.; Khodarahmi, E. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents: A review. J. Res. Med. Sci., 2015, 20, 1094-1104.
[28]
Asif, M. Mini review on important biological properties of benzofuran derivatives. J. Anal. Pharm. Res., 2016, 3(2), 00050.
[http://dx.doi.org/10.15406/japlr.2016.03.00050]
[29]
Jagtap, S.V.; Khan, A.A. Synthesis and biological activities of aurones: A review. Int. J. Pure App. Biosci., 2016, 4(2), 137-155.
[http://dx.doi.org/10.18782/2320-7051.2230]
[30]
Heravi, M.M.; Zadsirjan, V.; Hamidi, H.; Amiri, P.H.T. Total synthesis of natural products containing benzofuran rings. RSC Advances, 2017, 7, 24470-24521.
[http://dx.doi.org/10.1039/C7RA03551A]
[31]
More, K.R. Review on synthetic routes for synthesis of benzofuran-based compounds. J. Chem. Pharm. Res., 2017, 9(5), 210-220.
[32]
Sangeetha, B.; Deepti, R. Synthetic routes and biological activities of benzofuran and its derivatives: A review. Lett. Org. Chem., 2017, 14(6), 381-402.
[33]
Kadieva, M.G.; Oganesyan, E.T. Methods for the synthesis of benzofuran derivatives. Chem. Heterocycl. Compd., 1997, 33, 1245-1258.
[http://dx.doi.org/10.1007/BF02320323]
[34]
Sidhu, P.S. One-pot synthesis protocol for highly functionalized benzofuran scaffold. Postdoc. J. Res., 2013, 1, 31-36.
[35]
Abu-Hashem, A.A.; Hussein, H.A.R.; Ali, A.S.; Gouda, M.A. Synthesis of benzofuran derivatives via different methods. Syn. Comm, 2014, 44, 1-28.
[36]
Sharifi, A.; Abaee, M.S.; Tavakkoli, A.; Mirzaei, M. An efficient and general procedure for room-temperature synthesis of benzofurans under solvent-free conditions using KF/Al2O3. J. Iran. Chem. Soc., 2008, 5, S113-S117.
[http://dx.doi.org/10.1007/BF03246499]
[37]
Kumar, D.B.; Drakash, G.K.; Kumaraswamy, M.N.; Nandeshwarappa, B.P.; Sherigara, B.S.; Mahadevan, K.M. Synthesis and antimicrobial investigation of some novel phenyl and diazenyl ethanone derivatives of benzofurane azetidinone. Indian J. Chem., 2007, 46B(2), 336-343.
[38]
Wang, J.R.; Manabe, K. Hydroxyterphenylphoshine-palladium catalyst for benzo[b]furan synthesis from 2-chlorophenols. bifunctional ligand strategy for cross-coupling of chloroarenes. J. Org. Chem., 2010, 75(15), 5340-5342.
[http://dx.doi.org/10.1021/jo1007948] [PMID: 20578763]
[39]
Thalji, R.K.; Aiyar, N.; Davenport, E.A.; Erhardt, J.A.; Kallal, L.A.; Morrow, D.M.; Senadhi, S.; Burns-Kurtis, C.L.; Marino, J.P., Jr Benzofuran-substituted urea derivatives as novel P2Y(1) receptor antagonists. Bioorg. Med. Chem. Lett., 2010, 20(14), 4104-4107.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.072] [PMID: 20542694]
[40]
Wang, S.; Li, P.; Yu, L.; Wang, L. Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans. Org. Lett., 2011, 13(22), 5968-5971.
[http://dx.doi.org/10.1021/ol202383z] [PMID: 22007879]
[41]
Fischer, J.; Savage, G.P.; Coster, M.J. A concise route to dihydrobenzo[b]furans: formal total synthesis of (+)-lithospermic acid. Org. Lett., 2011, 13(13), 3376-3379.
[http://dx.doi.org/10.1021/ol201130h] [PMID: 21648396]
[42]
Li, C.; Zhang, Y.; Li, P.; Wang, L. Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols. J. Org. Chem., 2011, 76(11), 4692-4696.
[http://dx.doi.org/10.1021/jo200317f] [PMID: 21542613]
[43]
Luo, Y.; Wu, J. A new insight into palladium-catalyzed reaction of 2-alkynylphenol with carbon monoxide. Org. Lett., 2011, 13(21), 5858-5861.
[http://dx.doi.org/10.1021/ol202478u] [PMID: 21988411]
[44]
Lee, N.L.; Lee, J.J.; Kim, J-K.; Jun, J-G. Ailanthoidol derivatives and their anti-inflammatory effects. Bull. Korean Chem. Soc., 2012, 33, 1907-1912.
[http://dx.doi.org/10.5012/bkcs.2012.33.6.1907]
[45]
Bao, X.; Lu, S.; Liow, J-S.; Zoghbi, S.S.; Jenko, K.J.; Clark, D.T.; Gladding, R.L.; Innis, R.B.; Pike, V.W. Radiosynthesis and evaluation of an (18)F-labeled positron emission tomography (PET) radioligand for brain histamine subtype-3 receptors based on a nonimidazole 2-aminoethylbenzofuran chemotype. J. Med. Chem., 2012, 55(5), 2406-2415.
[http://dx.doi.org/10.1021/jm201690h] [PMID: 22313227]
[46]
Byers, P.M.; Rashid, J.I.; Mohamed, R.K.; Alabugin, I.V. Polyaromatic ribbon/benzofuran fusion via consecutive endo cyclizations of enediynes. Org. Lett., 2012, 14(23), 6032-6035.
[http://dx.doi.org/10.1021/ol302922t] [PMID: 23190310]
[47]
Kitamura, T.; Otsubo, K. Palladium-catalyzed intramolecular hydroarylation of 4-benzofuranyl alkynoates. Approach to angelicin derivatives. J. Org. Chem., 2012, 77(6), 2978-2982.
[http://dx.doi.org/10.1021/jo300021a] [PMID: 22372387]
[48]
Leibeling, M.; Pawliczek, M.; Kratzert, D.; Stalke, D.; Werz, D.B. A ridge walk between reaction modes: an unprecedented Pd-catalyzed domino sequence of diynyl-substituted bromoarenes. Org. Lett., 2012, 14(1), 346-349.
[http://dx.doi.org/10.1021/ol2030923] [PMID: 22166119]
[49]
Wang, X.; Liu, M.; Xu, L.; Wang, Q.; Chen, J.; Ding, J.; Wu, H. Palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles: synthesis of alkyl aryl ketones, diketone compounds, and 2-arylbenzo[b]furans. J. Org. Chem., 2013, 78(11), 5273-5281.
[http://dx.doi.org/10.1021/jo400433m] [PMID: 23668296]
[50]
Wang, X.; Wang, X.; Liu, M.; Xu, L.; Ding, J.; Chen, J.; Wu, H. Palladium-catalyzed reaction of arylboronic acids with aliphatic nitriles: Synthesis of alkyl aryl ketones and 2-Arylbenzofurans. Synthesis, 2013, 45, 2241-2244.
[http://dx.doi.org/10.1055/s-0033-1338909]
[51]
Yuan, H.; Bi, K.J.; Li, B.; Yue, R.C.; Ye, J.; Shen, Y.H.; Shan, L.; Jin, H.Z.; Sun, Q.Y.; Zhang, W.D. Construction of 2-substituted-3-functionalized benzofurans via intramolecular Heck coupling: application to enantioselective total synthesis of daphnodorin B. Org. Lett., 2013, 15(18), 4742-4745.
[http://dx.doi.org/10.1021/ol4021095] [PMID: 24007373]
[52]
Yuan, W.; Ma, S. Benzofuran derivatives from alkynyl-substituted benzynes and aryl halides. Org. Lett., 2014, 16(1), 193-195.
[http://dx.doi.org/10.1021/ol4032254] [PMID: 24387317]
[53]
Thirupathi, N.; Babu, M.H.; Dwivedi, V.; Kant, R.; Reddy, M.S. Palladium-catalyzed tandem intramolecular oxy/amino-palladation/isocyanide insertion: synthesis of α-benzofuranyl/indolylacetamides. Org. Lett., 2014, 16(11), 2908-2911.
[http://dx.doi.org/10.1021/ol501048x] [PMID: 24819584]
[54]
Gao, Y.; Xiong, W.; Chen, H.; Wu, W.; Peng, J.; Gao, Y.; Jiang, H. Pd-catalyzed highly regio- and stereoselective formation of C-C double bonds: An efficient method for the synthesis of benzofuran-, dihydrobenzofuran-, and indoline-containing alkenes. J. Org. Chem., 2015, 80(15), 7456-7467.
[http://dx.doi.org/10.1021/acs.joc.5b01024] [PMID: 26158340]
[55]
Rajesh, M.; Thirupathi, N.; Reddy, T.J.; Kanojiya, S.; Reddy, M.S. Pd-catalyzed isocyanide assisted reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols for 2-alkyl/benzyl benzofurans and their useful oxidative derivatization. J. Org. Chem., 2015, 80(24), 12311-12320.
[http://dx.doi.org/10.1021/acs.joc.5b02204] [PMID: 26599200]
[56]
Mariusz, J.B. A convenient synthesis of 2-arylbenzo[b]furans from aryl halides and 2-halophenols by catalytic one-pot cascade method. ACS Catal., 2016, 6, 2429-2434.
[http://dx.doi.org/10.1021/acscatal.6b00190]
[57]
Funes-Ardoiz, I.; González, J.; Santamaría, J.; Sampedro, D. Understanding the mechanism of the divergent reactivity of non-heteroatom-stabilized chromium carbene complexes with furfural imines: Formation of benzofurans and azetines. J. Org. Chem., 2016, 81(4), 1565-1570.
[http://dx.doi.org/10.1021/acs.joc.5b02729] [PMID: 26799934]
[58]
Kumar, A.; Gangwar, M.K.; Prakasham, A.P.; Mhatre, D.; Kalita, A.Ch.; Ghosh, P. Accessing a biologically relevant benzofuran skeleton by a one-pot tandem heck alkynylation/cyclization reaction using well-defined palladium N-heterocyclic carbene complexes. Inorg. Chem., 2016, 55(6), 2882-2893.
[http://dx.doi.org/10.1021/acs.inorgchem.5b02727] [PMID: 26928799]
[59]
Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. Assembly of 3-sulfenylbenzofurans and 3-sulfenylindoles by palladium-catalyzed cascade annulation/arylthiolation reaction. J. Org. Chem., 2016, 81(7), 2875-2887.
[http://dx.doi.org/10.1021/acs.joc.6b00162] [PMID: 26980622]
[60]
Paul, K.; Jalal, S.; Kundal, S.; Jana, U. Synthesis of fused dibenzofuran derivatives via palladium-catalyzed domino C-C Bond formation and iron-catalyzed cycloisomerization/aromatization. J. Org. Chem., 2016, 81(3), 1164-1174.
[http://dx.doi.org/10.1021/acs.joc.5b02637] [PMID: 26728954]
[61]
Varela-Fernández, A.; González-Rodríguez, C.; Varela, J.A.; Castedo, L.; Saá, C. Cycloisomerization of aromatic homo- and bis-homopropargylic alcohols via catalytic Ru vinylidenes: formation of benzofurans and isochromenes. Org. Lett., 2009, 11(22), 5350-5353.
[http://dx.doi.org/10.1021/ol902212h] [PMID: 19860408]
[62]
Lee, D.H.; Kwon, K.H.; Yi, C.S. Dehydrative C-H alkylation and alkenylation of phenols with alcohols: expedient synthesis for substituted phenols and benzofurans. J. Am. Chem. Soc., 2012, 134(17), 7325-7328.
[http://dx.doi.org/10.1021/ja302710v] [PMID: 22494241]
[63]
Rit, R.K.; Ghosh, K.; Mandal, R.; Sahoo, A.K. Ruthenium-catalyzed intramolecular hydroarylation of arenes and mechanistic study: Synthesis of dihydrobenzofurans, indolines, and chromans. J. Org. Chem., 2016, 81(18), 8552-8560.
[http://dx.doi.org/10.1021/acs.joc.6b01734] [PMID: 27548436]
[64]
Xia, Z.; Khaled, O.; Mouriès-Mansuy, V.; Ollivier, C.; Fensterbank, L. Dual photoredox/gold catalysis arylative cyclization of o-alkynylphenols with aryldiazonium salts: A flexible synthesis of benzofurans. J. Org. Chem., 2016, 81(16), 7182-7190.
[http://dx.doi.org/10.1021/acs.joc.6b01060] [PMID: 27362460]
[65]
Shibata, T.; Hashimoto, Y.K.; Otsuka, M.; Tsuchikama, K.; Endo, K. Ir(III)-catalyzed room-temperature synthesis of multisubstituted benzofurans initiated by C-H activation of α-aryloxy ketones. Synlett, 2011, 14, 2075-2079.
[http://dx.doi.org/10.1055/s-0030-1260981]
[66]
Anxionnat, B.; Gomez Pardo, D.; Ricci, G.; Rossen, K.; Cossy, J. Iridium-catalyzed hydrogen transfer: synthesis of substituted benzofurans, benzothiophenes, and indoles from benzyl alcohols. Org. Lett., 2013, 15(15), 3876-3879.
[http://dx.doi.org/10.1021/ol401610e] [PMID: 23859265]
[67]
Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. CuBr-catalyzed coupling of N-tosylhydrazones and terminal alkynes: Synthesis of benzofurans and indoles. Org. Lett., 2011, 13(5), 968-971.
[http://dx.doi.org/10.1021/ol103009n] [PMID: 21268646]
[68]
Hirano, K.; Satoh, T.; Miura, M. Copper-catalyzed annulative amination of ortho-alkynylphenols with hydroxylamines: synthesis of 3-aminobenzofurans by umpolung amination strategy. Org. Lett., 2011, 13(9), 2395-2397.
[http://dx.doi.org/10.1021/ol200651r] [PMID: 21449554]
[69]
Ameta, K.L.; Nitu, S.R.; Biresh, K.; Edith, S.M.; Manuela, V.; Robert, H.G.; Verma, B.L. Synthesis and trypanocidal evaluation of some novel 2-(substituted benzylidene)-5, 7-dibromo-6-hydroxy-1-benzofuran-3(2h)-ones. Int. J. Org. Chem. (Irvine), 2012, 2, 295-301.
[http://dx.doi.org/10.4236/ijoc.2012.223040]
[70]
Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. An annulative electrophilic amination approach to 3-aminobenzoheteroles. J. Org. Chem., 2012, 77(1), 617-625.
[http://dx.doi.org/10.1021/jo202207s] [PMID: 22132905]
[71]
Ye, S.; Liu, G.; Pu, S.; Wu, J. Synthesis of 2-(polyfluoroaryl)benzofurans via a copper(I)-catalyzed reaction of 2-(2,2-dibromovinyl)phenol with polyfluoroarene. Org. Lett., 2012, 14(1), 70-73.
[http://dx.doi.org/10.1021/ol202858f] [PMID: 22136654]
[72]
Zhu, R.; Wei, J.; Shi, Z. Benzofuran synthesis via copper-mediated oxidative annulation of phenols and unactivated internal alkynes. Chem. Sci., 2013, 4, 3706-3711.
[http://dx.doi.org/10.1039/c3sc51489g]
[73]
Wan, J.P.; Wang, H.; Liu, Y.; Ding, H. Synthesis of 2-vinylbenzofurans via the copper-catalyzed multicomponent reactions involving an oxa-Michael/arylation/vinylation cascade. Org. Lett., 2014, 16(19), 5160-5163.
[http://dx.doi.org/10.1021/ol502506g] [PMID: 25250977]
[74]
Liu, Y.; Wang, H.; Wan, J.P. Copper-catalyzed, C-C coupling-based one-pot tandem reactions for the synthesis of benzofurans using o-iodophenols, acyl chlorides, and phosphorus ylides. J. Org. Chem., 2014, 79(21), 10599-10604.
[http://dx.doi.org/10.1021/jo5017508] [PMID: 25279735]
[75]
Hao, H.; Chen, W.; Zhu, J.; Lu, C.; Shen, Y. Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents. Eur. J. Med. Chem., 2015, 102, 277-287.
[http://dx.doi.org/10.1016/j.ejmech.2015.07.048] [PMID: 26291037]
[76]
Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H. Palladium-catalyzed tandem annulation: a strategy to construct 2,3-difunctionalized benzofuran derivatives in ionic liquids. J. Org. Chem., 2015, 80(8), 3870-3879.
[http://dx.doi.org/10.1021/acs.joc.5b00154] [PMID: 25781033]
[77]
Ren, H.; Wang, P.; Wang, L.; Tang, Y. Catalytic asymmetric synthesis of 3-hydroxy-3-trifluoromethyl benzofuranones via tandem Friedel-Crafts/lactonization reaction. Org. Lett., 2015, 17(19), 4886-4889.
[http://dx.doi.org/10.1021/acs.orglett.5b02440] [PMID: 26400069]
[78]
Xu, T.; Zhang, E.; Wang, D.; Wang, Y.; Zou, Y. Cu-catalyzed consecutive hydroxylation and aerobic oxidative cycloetherification under microwave conditions: Entry to 2-arylbenzofuran-3-carboxylic acids. J. Org. Chem., 2015, 80(9), 4313-4324.
[http://dx.doi.org/10.1021/jo502802k] [PMID: 25836742]
[79]
You, W.; Brown, M.K. Catalytic enantioselective diarylation of alkenes. J. Am. Chem. Soc., 2015, 137(46), 14578-14581.
[http://dx.doi.org/10.1021/jacs.5b10176] [PMID: 26565926]
[80]
Song, Z.J.; Tan, L.; Liu, G.; Ye, H.; Dong, J. Concise Cu (I) catalyzed synthesis of substituted benzofurans via a tandem SNAr/C–O coupling process. Org. Process Res. Dev., 2016, 20, 1088-1092.
[http://dx.doi.org/10.1021/acs.oprd.6b00141]
[81]
Zhang, L.; Peng, Z.; Wen, Q.; Li, X.; Lu, P.; Wang, Y. Copper-catalyzed preparation of 2-aryl-3-cyanobenzofurans with bright blue photoluminescence. Org. Lett., 2016, 18(4), 728-731.
[http://dx.doi.org/10.1021/acs.orglett.5b03704] [PMID: 26835551]
[82]
Rehan, M.; Nallagonda, R.; Das, B.G.; Meena, T.; Ghorai, P. Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols. J. Org. Chem., 2017, 82(7), 3411-3424.
[http://dx.doi.org/10.1021/acs.joc.6b02752] [PMID: 28249386]
[83]
Prakash, H.S.; Satish, V. Synthesis and photochromic properties of benzofuran-phenanthrene and benzofuran–pyrene hybrids. RSC Advances, 2014, 4, 25747.
[http://dx.doi.org/10.1039/C4RA02435D]
[84]
Okamoto, R.; Okazaki, E.; Noguchi, K.; Tanaka, K. Rhodium-catalyzed olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade. Org. Lett., 2011, 13(18), 4894-4897.
[http://dx.doi.org/10.1021/ol201986e] [PMID: 21866888]
[85]
Lu, P.; Mailyan, A.; Gu, Z.; Guptill, D.M.; Wang, H.; Davies, H.M.L.; Zakarian, A. Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization. J. Am. Chem. Soc., 2014, 136(51), 17738-17749.
[http://dx.doi.org/10.1021/ja510573v] [PMID: 25409033]
[86]
Zhou, Z.; Liu, G.; Chen, Y.; Lu, X. Cascade synthesis of 3-alkylidene dihydrobenzofuran derivatives via Rhodium(III)-catalyzed redox-neutral C-H functionalization/cyclization. Org. Lett., 2015, 17(23), 5874-5877.
[http://dx.doi.org/10.1021/acs.orglett.5b03060] [PMID: 26567588]
[87]
Ma, J.; Chen, K.; Fu, H.; Zhang, L.; Wu, W.; Jiang, H.; Zhu, S. Dual catalysis: Proton/metal-catalyzed tandem benzofuran annulation/carbene transfer reaction. Org. Lett., 2016, 18(6), 1322-1325.
[http://dx.doi.org/10.1021/acs.orglett.6b00260] [PMID: 26950391]
[88]
Kanno, H.; Nakamura, K.; Noguchi, K.; Shibata, Y.; Tanaka, K. Rhodium-catalyzed cycloisomerization of 2-silylethynyl phenols and anilines via 1,2-silicon migration. Org. Lett., 2016, 18(7), 1654-1657.
[http://dx.doi.org/10.1021/acs.orglett.6b00529] [PMID: 27002692]
[89]
Wu, F.; Bai, R.; Gu, Y. Synthesis of benzofurans from ketones and 1,4‐benzoquinones. Adv. Synth. Catal., 2016, 358, 2307-2316.
[http://dx.doi.org/10.1002/adsc.201600048]
[90]
Ye, Y.; Fan, R. Silver-catalyzed synthesis of 4-substituted benzofurans via a cascade oxidative coupling-annulation protocol. Chem. Commun. (Camb.), 2011, 47(19), 5626-5628.
[http://dx.doi.org/10.1039/c1cc10137d] [PMID: 21483903]
[91]
Fan, H-F.; Ren, Y-M.; Wu, X-L.; Wang, Q-A. Synthesis and cytotoxicity of novel benzofuran neolignan derivatives. J. Chem. Res., 2010, 34, 233-235.
[http://dx.doi.org/10.3184/030823410X12709997864719]
[92]
Pei, T.; Chen, C.Y.; DiMichele, L.; Davies, I.W. Controlled synthesis of 2- and 3-substituted benzo[b]furans. Org. Lett., 2010, 12(21), 4972-4975.
[http://dx.doi.org/10.1021/ol102123u] [PMID: 20873816]
[93]
Liu, Y.; Jacobs, H.K.; Gopalan, A.S. A new approach to fused furan ring systems and benzofurans: Intramolecular cyclization reactions of unsaturated acyloxy sulfone derivatives. Tet. Lett., 2010, 52, 2935-2939.
[http://dx.doi.org/10.1016/j.tetlet.2011.03.120]
[94]
Bhaskar, S.D.; Shankaraiah, G.K.; Namdev, T.K.; Santosh, S.C.; Baseer, M.S.; Ragini, G.B.; Vishwas, D.J. Synthesis and antimicrobial evaluation of 2-(2-butyl- 4-chloro-1H-imidazol-5-yl-methylene)-substituted-benzofuran-3-ones. Org. Commun., 2010, 3(2), 22-29.
[95]
Liu, Y.; Qian, J.; Lou, S.; Xu, Z. Gold(III)-catalyzed tandem reaction of O-arylhydroxylamines with 1,3-dicarbonyl compounds: highly selective synthesis of 3-carbonylated benzofuran derivatives. J. Org. Chem., 2010, 75(18), 6300-6303.
[http://dx.doi.org/10.1021/jo101357d] [PMID: 20707352]
[96]
Kumari, A.L.S.; Swamy, K.C.K. Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation. J. Org. Chem., 2015, 80(8), 4084-4096.
[http://dx.doi.org/10.1021/acs.joc.5b00415] [PMID: 25793444]
[97]
Obata, T.; Suzuki, S.; Nakagawa, A.; Kajihara, R.; Noguchi, K.; Saito, A. Gold-catalyzed domino synthesis of functionalized benzofurans and tetracyclic isochromans via formal carboalkoxylation. Org. Lett., 2016, 18(16), 4136-4139.
[http://dx.doi.org/10.1021/acs.orglett.6b02159] [PMID: 27482726]
[98]
Buccini, M.; Piggott, M.J. A four-step total synthesis of radermachol. Org. Lett., 2014, 16(9), 2490-2493.
[http://dx.doi.org/10.1021/ol500862w] [PMID: 24745304]
[99]
Yadav, P.; Singh, P.; Tewari, A.K. Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs. Bioorg. Med. Chem. Lett., 2014, 24(10), 2251-2255.
[http://dx.doi.org/10.1016/j.bmcl.2014.03.087] [PMID: 24745964]
[100]
Allegretti, P.A.; Huynh, K.; Ozumerzifon, T.J.; Ferreira, E.M. Lewis acid mediated vinylogous additions of enol nucleophiles into an α,β-unsaturated platinum carbene. Org. Lett., 2016, 18(1), 64-67.
[101]
Burgstahler, A.W.; Worden, L.R. Coumarone: Benzofuran. Org. Synth., 2003, 46, 28.
[102]
Perkin, W.H. XXIX.-On some new bromine derivatives of coumarin. J. Chem. Soc., 1870, 23, 368-371.
[http://dx.doi.org/10.1039/JS8702300368]
[103]
Jiang, X.; Liu, W.; Zhang, W.; Jiang, F.; Gao, Z.; Zhuang, H.; Fu, L. Synthesis and antimicrobial evaluation of new benzofuran derivatives. Eur. J. Med. Chem., 2011, 46(8), 3526-3530.
[http://dx.doi.org/10.1016/j.ejmech.2011.04.053] [PMID: 21570749]
[104]
Gao, W.; Liu, J.; Jiang, Y.; Li, Y. First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives. Beilstein J. Org. Chem., 2011, 7, 210-217.
[http://dx.doi.org/10.3762/bjoc.7.28] [PMID: 21445378]
[105]
Gao, W.; Jiang, Y.; Li, Y.; Li, F.; Yan, Y. A Novel and facile synthesis of 2‐(benzofuran‐2‐yl) benzo [h] quinoline‐3‐carboxylic acid derivatives. Chin. J. Chem., 2012, 30, 822-826.
[http://dx.doi.org/10.1002/cjoc.201100389]
[106]
Vidyashri, S.K.; Bhalchandra, M.H.; Geeta, K.P.; Agasimundin, Y. Synthesis and evaluation of 4-(1-benzofuran-2-yl)-1, 3-oxazole-2-amine and its derivatives. Int. J. Res. Pharm. Chem., 2012, 2, 32-36.
[107]
Cai, J.; Chen, J.; Cao, M.; Wang, P.; Feng, C.; Ji, M. Design, synthesis, and biological evaluation of benzofuran derivatives as ET receptor antagonists. Med. Chem. Res., 2013, 22, 5472-5480.
[http://dx.doi.org/10.1007/s00044-013-0542-3]
[108]
Devi, S.K.; Mishra, Y.K.; Ajay, M.C. Synthesis and photochemical study of 1- (3-methyl -6- hydroxy benzofuran-2-yl)-carbohydrazide-3- chloro -4- phenylazetidin-2-one. Int. J. Chem. Stu., 2014, 2, 25-30.
[109]
Mao, Z-W.; Zheng, X.; Lin, Y-P.; Hu, C-Y.; Wang, X-L.; Wan, C-P.; Rao, G-X. Design, synthesis and anticancer activity of novel hybrid compounds between benzofuran and N-aryl piperazine. Bioorg. Med. Chem. Lett., 2016, 26(15), 3421-3424.
[http://dx.doi.org/10.1016/j.bmcl.2016.06.055] [PMID: 27371110]
[110]
Contiero, F.; Jones, K.M.; Matts, E.A.; Porzelle, A.; Tomkinson, N.C.O. Direct preparation of benzofurans from O-arylhydroxylamines. Synlett, 2009, 18, 3003-3006.
[111]
Zhou, X.; Li, M.; Wang, X-B.; Wang, T.; Kong, L-Y. Synthesis of benzofuran derivatives via rearrangement and their inhibitory activity on acetylcholinesterase. Molecules, 2010, 15(12), 8593-8601.
[http://dx.doi.org/10.3390/molecules15128593] [PMID: 21116228]
[112]
Parekh, S.; Bhavsar, D.; Savant, M.; Thakrar, S.; Bavishi, A.; Parmar, M.; Vala, H.; Radadiya, A.; Pandya, N.; Serly, J.; Molnár, J.; Shah, A. Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro. Eur. J. Med. Chem., 2011, 46(5), 1942-1948.
[http://dx.doi.org/10.1016/j.ejmech.2011.02.045] [PMID: 21396744]
[113]
Singh, F.V.; Wirth, T. Oxidative rearrangements with hypervalent iodine reagents. Synthesis, 2013, 44, 1171-1177.
[http://dx.doi.org/10.1055/s-0031-1290588]
[114]
Shachan-Tov, S.; Frimer, A.A. Novel and convenient synthesis of benzofurans from dihydrocoumarins. J. Heterocycl. Chem., 2012, 49, 905-908.
[http://dx.doi.org/10.1002/jhet.896]
[115]
Nagaraju, M.; Gnana Deepthi, E.; Ashwini, C.; Vishnuvardhan, M.V.P.S.; Lakshma Nayak, V.; Chandra, R.; Ramakrishna, S.; Gawali, B.B. Synthesis and selective cytotoxic activity of novel hybrid chalcones against prostate cancer cells. Bioorg. Med. Chem. Lett., 2012, 22(13), 4314-4317.
[http://dx.doi.org/10.1016/j.bmcl.2012.05.016] [PMID: 22668451]
[116]
Yusifov, N.N.; Ismayilov, V.M.; Sadigova, N.D.; Kopylovich, M.N.; Mahmudov, K.T. A straightforward synthesis of 2(3),6,6-trimethyl- 6,7-dihydrobenzofuran-4(5H)-ones. Mendeleev Commun., 2013, 23, 292-293.
[http://dx.doi.org/10.1016/j.mencom.2013.09.019]
[117]
Schlosser, J.; Johannes, E.; Zindler, M.; Lemmerhirt, J.; Sommer, B.; Schütt, M.; Peifer, C. Novel synthesis of benzofuran-and indol-2-yl-methanamine derivatives. Tetrahedron Lett., 2014, 56, 89-94.
[http://dx.doi.org/10.1016/j.tetlet.2014.11.015]
[118]
Osyanin, V.A.; Osipov, D.V.; Demidov, M.R.; Klimochkin, Y.N. Potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent: access to 2-nitroarenofurans. J. Org. Chem., 2014, 79(3), 1192-1198.
[http://dx.doi.org/10.1021/jo402543s] [PMID: 24417319]
[119]
Danilkina, N.A.; Kulyashova, A.E.; Khlebnikov, A.F.; Bräse, S.; Balova, I.A. Electrophilic cyclization of aryldiacetylenes in the synthesis of functionalized enediynes fused to a heterocyclic core. J. Org. Chem., 2014, 79(19), 9018-9045.
[http://dx.doi.org/10.1021/jo501396s] [PMID: 25162655]
[120]
Lee, J.H.; Kim, M.; Kim, I. Palladium-catalyzed α-arylation of aryloxyketones for the synthesis of 2,3-disubstituted benzofurans. J. Org. Chem., 2014, 79(13), 6153-6163.
[http://dx.doi.org/10.1021/jo500885w] [PMID: 24856099]
[121]
Ma, G-H.; Tu, X-J.; Ning, Y.; Jiang, B.; Tu, S-J. Efficient domino strategy for the synthesis of polyfunctionalized benzofuran-4(5H)-ones and cinnoline-4-carboxamides. ACS Comb. Sci., 2014, 16(6), 281-286.
[http://dx.doi.org/10.1021/co5000097] [PMID: 24588380]
[122]
Shaikh, A.K; Varvounis, G. Novel synthesis of 3-substituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ. Org. Lett., 2014, 16(5), 1478-1481.
[http://dx.doi.org/10.1021/ol500290e] [PMID: 24571271]
[123]
Ye, X-.Y.; Morales, C.L.; Wang, Y.; Rossi, K.A.; Malmstrom, S.E.; Abousleiman, M.; Sereda, L.; Apedo, A.; Robl, J.A.; Miller, K.J.; Krupinski, J.; Wacker, D.A. Synthesis and structure-activity relationship of dihydrobenzofuran derivatives as novel human GPR119 agonists. Bioorg. Med. Chem. Lett., 2014, 24(11), 2539-2545.
[http://dx.doi.org/10.1016/j.bmcl.2014.03.096] [PMID: 24755425]
[124]
Salomé, C.; Ribeiro, N.; Chavagnan, T.; Thuaud, F.; Serova, M.; de Gramont, A.; Faivre, S.; Raymond, E.; Désaubry, L. Benzofuran derivatives as anticancer inhibitors of mTOR signaling. Eur. J. Med. Chem., 2014, 81, 181-191.
[http://dx.doi.org/10.1016/j.ejmech.2014.05.014] [PMID: 24836070]
[125]
Choi, M.; Jo, H.; Park, H.J.; Kumar, A.S.; Lee, J.; Yun, J.; Kim, Y.; Han, S.B.; Jung, J.K.; Cho, J.; Lee, K. Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB. Bioorg. Med. Chem. Lett., 2015, 25(12), 2545-2549.
[126]
Niu, G.; Liu, W.; Wu, J.; Zhou, B.; Chen, J.; Zhang, H.; Ge, J.; Wang, Y.; Xu, H.; Wang, P. Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications. J. Org. Chem., 2015, 80(6), 3170-3175.
[http://dx.doi.org/10.1021/acs.joc.5b00077] [PMID: 25692322]
[127]
Baharloo, F.; Moslemin, M.H.; Nadri, H.; Asadipour, A.; Mahdavi, M.; Emami, S.; Firoozpour, L.; Mohebat, R.; Shafiee, A.; Foroumadi, A. Benzofuran-derived benzylpyridinium bromides as potent acetylcholinesterase inhibitors. Eur. J. Med. Chem., 2015, 93, 196-201.
[http://dx.doi.org/10.1016/j.ejmech.2015.02.009] [PMID: 25681712]
[128]
Mostofi, M.; Mohammadi Ziarani, G.; Mahdavi, M.; Moradi, A.; Nadri, H.; Emami, S.; Alinezhad, H.; Foroumadi, A.; Shafiee, A. Synthesis and structure-activity relationship study of benzofuran-based chalconoids bearing benzylpyridinium moiety as potent acetylcholinesterase inhibitors. Eur. J. Med. Chem., 2015, 103, 361-369.
[http://dx.doi.org/10.1016/j.ejmech.2015.08.061] [PMID: 26363872]
[129]
Kurt, B.Z.; Gazioglu, I.; Basile, L.; Sonmez, F.; Ginex, T.; Kucukislamoglu, M.; Guccione, S. Potential of aryl-urea-benzofuranylthiazoles hybrids as multitasking agents in Alzheimer’s disease. Eur. J. Med. Chem., 2015, 102, 80-92.
[http://dx.doi.org/10.1016/j.ejmech.2015.07.005] [PMID: 26244990]
[130]
Reddi, Y.; Sunoj, R.B. Asymmetric dual-catalytic cascade by chiral n-heterocyclic carbene and quinuclidine: Mechanism and origin of enantioselectivity in benzofuranone formation. ACS Catal., 2015, 5, 1596-1603.
[http://dx.doi.org/10.1021/cs502006x]
[131]
Xue, S-T.; Guo, H-F.; Liu, M-J.; Jin, J.; Ju, D-H.; Liu, Z-Y.; Li, Z-R. Synthesis of a novel class of substituted benzothiophene or benzofuran derivatives as BMP-2 up-regulators and evaluation of the BMP-2-up-regulating effects in vitro and the effects on glucocorticoid-induced osteoporosis in rats. Eur. J. Med. Chem., 2015, 96, 151-161.
[http://dx.doi.org/10.1016/j.ejmech.2015.04.016] [PMID: 25874339]
[132]
Pokhodylo, N.T.; Shyyka, O.Y.; Matiychuk, V.S.; Obushak, M.D. New convenient strategy for annulation of pyrimidines to thiophenes or furans via the one-pot multistep cascade reaction of 1H-tetrazoles with aliphatic amines. ACS Comb. Sci., 2015, 17(7), 399-403.
[http://dx.doi.org/10.1021/co5001376] [PMID: 26091557]
[133]
Romagnoli, R.; Baraldi, P.G.; Salvador, M.K.; Prencipe, F.; Lopez-Cara, C.; Schiaffino Ortega, S.; Brancale, A.; Hamel, E.; Castagliuolo, I.; Mitola, S.; Ronca, R.; Bortolozzi, R.; Porcù, E.; Basso, G.; Viola, G. Design, synthesis, in vitro, and in vivo anticancer and antiangiogenic activity of novel 3-arylaminobenzofuran derivatives targeting the colchicine site on tubulin. J. Med. Chem., 2015, 58(7), 3209-3222.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00155] [PMID: 25785605]
[134]
He, S.; Jain, P.; Lin, B.; Ferrer, M.; Hu, Z.; Southall, N.; Hu, X.; Zheng, W.; Neuenswander, B.; Cho, C-H.; Chen, Y.; Worlikar, S.A.; Aubé, J.; Larock, R.C.; Schoenen, F.J.; Marugan, J.J.; Liang, T.J.; Frankowski, K.J. High-throughput screening, discovery, and optimization to develop a benzofuran class of hepatitis c virus inhibitors. ACS Comb. Sci., 2015, 17(10), 641-652.
[http://dx.doi.org/10.1021/acscombsci.5b00101] [PMID: 26332742]
[135]
Liang, Z.; Xu, H.; Tian, Y.; Guo, M.; Su, X.; Guo, C. Design, synthesis and antifungal activity of novel benzofuran-triazole hybrids. Molecules, 2016, 21, 732-742.
[http://dx.doi.org/10.3390/molecules21060732]
[136]
Ashok, S.K.; Mehnaz, M.K.; Vishal, M.B.; Sanna, K.B.; Rajashri, R.N.; Anil, K.S.; Siddiqui, H.H. Design, synthesis and evaluation of benzofuran-acetamide scaffold as potential anticonvulsant agent. Acta Pharm., 2016, 66, 353-372.
[http://dx.doi.org/10.1515/acph-2016-0023] [PMID: 27383885]
[137]
Vincetti, P.; Brianza, A.; Scalacci, N.; Costantino, G.; Castagnolo, D.; Radi, M. Tet; Lett, 2016.
[138]
Mashraqui, S.H.; Ghadigaonkar, S.G.; Ghorpade, S. Novel bipolar diaryloxadiazole-benzofuran conjugates: Synthesis, optical, electrochemical and thermal studies. Indian J. Chem., 2016, 55B, 368-373.
[139]
Khoeiniha, R.; Olyaei, A.; Saraei, M. Water‐based synthesis of novel 6, 7‐dihydrobenzofuran‐4 (5H)‐ones. J. Heterocycl. Chem., 2017, 54(3), 1746-1750.
[140]
Li, Y.; Zhuoma, B.; Gao, W. A novel synthesis of 2‐ferrocenoyl‐substituted iodobenzofurans. J. Heterocyclic. Chem., 2017, 54(1), 764-768.
[141]
Cheng, J.; McCorvy, J.D.; Giguere, P.M.; Zhu, H.; Kenakin, T.; Roth, B.L.; Kozikowski, A.P. Design and discovery of functionally selective serotonin 2C (5-HT2C) receptor agonists. J. Med. Chem., 2016, 59(21), 9866-9880.
[http://dx.doi.org/10.1021/acs.jmedchem.6b01194] [PMID: 27726356]
[142]
Baiceanu, E.; Nguyen, K-A.; Gonzalez-Lobato, L.; Nasr, R.; Baubichon-Cortay, H.; Loghin, F.; Le Borgne, M.; Chow, L.; Boumendjel, A.; Peuchmaur, M.; Falson, P. 2-Indolylmethylenebenzofuranones as first effective inhibitors of ABCC2. Eur. J. Med. Chem., 2016, 122, 408-418.
[http://dx.doi.org/10.1016/j.ejmech.2016.06.039] [PMID: 27393949]
[143]
Wakabayashi, T.; Tokunaga, N.; Tokumaru, K.; Ohra, T.; Koyama, N.; Hayashi, S.; Yamada, R.; Shirasaki, M.; Inui, Y.; Tsukamoto, T. Discovery of benzofuran derivatives that collaborate with Insulin-Like Growth Factor 1 (IGF-1) to promote neuroprotection. J. Med. Chem., 2016, 59(10), 5109-5114.
[http://dx.doi.org/10.1021/acs.jmedchem.6b00191] [PMID: 27163512]
[144]
Delogu, G.L.; Matos, M.J.; Fanti, M.; Era, B.; Medda, R.; Pieroni, E.; Fais, A.; Kumar, A.; Pintus, F. 2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling. Bioorg. Med. Chem. Lett., 2016, 26(9), 2308-2313.
[http://dx.doi.org/10.1016/j.bmcl.2016.03.039] [PMID: 26995529]
[145]
Kise, N.; Hamada, Y.; Sakurai, T. Electroreductive intermolecular coupling of coumarins with benzophenones: Synthesis of 4-(2-hydroxyphenyl)-5,5-diaryl-γ-butyrolactones, 2-(2,2-diaryl-2,3-dihydrobenzofuran-3-yl)acetic acids, and 4-(diarylmethyl) coumarins. J. Org. Chem., 2016, 81(22), 11043-11056.
[http://dx.doi.org/10.1021/acs.joc.6b02056] [PMID: 27704835]
[146]
Liang, G-B.; Zhou, C.; Huo, X.; Wang, H.; Yang, X.; Huang, S.; Wang, H.; Wilkinson, H.; Luo, L.; Tang, W.; Sutton, D.; Li, H.; Zaller, D.; Meinke, P.T. Discovery of novel dihydrobenzofuran cyclopropane carboxylic acid based calcium sensing receptor antagonists for the treatment of osteoporosis. Bioorg. Med. Chem. Lett., 2016, 26(16), 4077-4080.
[http://dx.doi.org/10.1016/j.bmcl.2016.06.073] [PMID: 27397499]
[147]
Lombardo, M.; Bender, K.; London, C.; Plotkin, M.A.; Kirkland, M.; Mane, J.; Pachanski, M.; Geissler, W.; Cummings, J.; Habulihaz, B.; Akiyama, T.E.; Di Salvo, J.; Madeira, M.; Pols, J.; Powles, M.A.; Finley, M.F.; Johnson, E.; Roussel, T.; Uebele, V.N.; Crespo, A.; Leung, D.; Alleyne, C.; Trusca, D.; Lei, Y.; Howard, A.D.; Ujjainwalla, F.; Tata, J.R.; Sinz, C.J. Discovery of benzofuran propanoic acid GPR120 agonists: From uHTS hit to mechanism-based pharmacodynamic effects. Bioorg. Med. Chem. Lett., 2016, 26(23), 5724-5728.
[http://dx.doi.org/10.1016/j.bmcl.2016.10.054] [PMID: 27815121]
[148]
Wang, Y.; Chen, F.; Di, H.; Xu, Y.; Xiao, Q.; Wang, X.; Wei, H.; Lu, Y.; Zhang, L.; Zhu, J.; Sheng, C.; Lan, L.; Li, J. Discovery of potent benzofuran-derived diapophytoene desaturase (CrtN) inhibitors with enhanced oral bioavailability for the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infections. J. Med. Chem., 2016, 59(7), 3215-3230.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01984] [PMID: 26999509]
[149]
Seo, Y.H.; Damodar, K.; Kim, J-K.; Jun, J-G. Synthesis and biological evaluation of 2-aroylbenzofurans, rugchalcones A, B and their derivatives as potent anti-inflammatory agents. Bioorg. Med. Chem. Lett., 2016, 26(6), 1521-1524.
[http://dx.doi.org/10.1016/j.bmcl.2016.02.023] [PMID: 26898337]
[150]
Yang, Y-R.; Wei, J-L.; Mo, X-F.; Yuan, Z-W.; Wang, J-L.; Zhang, C.; Xie, Y-Y.; You, Q-D.; Sun, H-P. Discovery and optimization of new benzofuran derivatives against p53-independent malignant cancer cells through inhibition of HIF-1 pathway. Bioorg. Med. Chem. Lett., 2016, 26(11), 2713-2718.
[http://dx.doi.org/10.1016/j.bmcl.2016.03.112] [PMID: 27101893]
[151]
Qin, Z.; Liu, W.; Wang, D.; He, Z. Phosphine-catalyzed (4 + 1) annulation of o-hydroxyphenyl and o-aminophenyl ketones with allylic carbonates: Syntheses and transformations of 3-hydroxy-2,3-disubstituted dihydrobenzofurans and indolines. J. Org. Chem., 2016, 81(11), 4690-4700.
[http://dx.doi.org/10.1021/acs.joc.6b00596] [PMID: 27166729]
[152]
Singh, L.; Pressly, B.; Mengeling, B.J.; Fettinger, J.C.; Furlow, J.D.; Lein, P.J.; Wulff, H.; Singh, V. Chasing the elusive benzofuran impurity of the THR antagonist NH-3: Synthesis, isotope labeling, and biological activity. J. Org. Chem., 2016, 81(5), 1870-1876.
[http://dx.doi.org/10.1021/acs.joc.5b02665] [PMID: 26849160]
[153]
Siddheshwar, K.B.; Jopaul, M; Ramasastry, S.S.V. Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of β-pyrones. Chem. Commun. (Camb.), 2016, 52, 5569-5572.
[http://dx.doi.org/10.1039/C6CC01016D] [PMID: 27019948]
[154]
Lavanya, A.; Sribalan, R.; Padmini, V.; Sau, J. Synthesis and biological evaluation of new benzofuran carboxamide derivatives. Chem. Soc., 2017, 21(3), 277-285.
[155]
Chen, C-Y.; Lin, C-M.; Lin, H-C.; Huang, C-F.; Lee, C-Y.; Si Tou, T-C.; Hung, C-C.; Chang, C-S. Structure-activity relationship study of novel 2-aminobenzofuran derivatives as P-glycoprotein inhibitors. Eur. J. Med. Chem., 2017, 125, 1023-1035.
[http://dx.doi.org/10.1016/j.ejmech.2016.08.044] [PMID: 27810590]

Rights & Permissions Print Cite
Article Metrics
23
© 2024 Bentham Science Publishers | Privacy Policy