Benzofuran as a promising scaffold for the synthesis of novel antimicrobial agents

References

• Alam MA. Antibacterial pyrazoles: tackling resistant bacteria. Future Med Chem. 2022;14(5):343–362.
   PubMed Web of Science ®Google Scholar
• Cossy J, Guerinot A. Natural products containing oxygen heterocycles—Synthetic advances between 1990 and 2015. Adv Heterocycl Chem. 2016;119:107–142.
   Web of Science ®Google Scholar
• Chand K, Hiremathad A, Singh M, et al. A review on antioxidant potential of bioactive heterocycle benzofuran: natural and synthetic derivatives. Pharmacol Rep. 2017;69(2):281–295.
   PubMed Web of Science ®Google Scholar
• Miao YH, Hu YH, Yang J, et al. Natural source, bioactivity and synthesis of benzofuran derivatives. RSC Adv. 2019;9(47):27510–27540.
   PubMed Web of Science ®Google Scholar
• Radadiya A, Shah A. Bioactive benzofuran derivatives: an insight on lead developments, radioligands and advances of the last decade. Eur J Med Chem. 2015;97:356–376.
   PubMed Web of Science ®Google Scholar
• Nevagi RJ, Dighe SN, Dighe SN. Biological and medicinal significance of benzofuran. Eur J Med Chem. 2015;97:561–581.
   PubMed Web of Science ®Google Scholar
• Carrasco MP, Newton AS, Gonçalves L, et al. Probing the aurone scaffold against Plasmodium falciparum: design, synthesis and antimalarial activity. Eur J Med Chem. 2014;80:523–534.
   PubMed Web of Science ®Google Scholar
• Jardosh HH, Patel MP. Antimicrobial and antioxidant evaluation of new quinolone based aurone analogs. Arab J Chem. 2017;10:3781–3791.
   Web of Science ®Google Scholar
• Li Y, Bao L, Song B, et al. A new benzoquinone and a new benzofuran from the edible mushroom Neolentinus lepideus and their inhibitory activity in NO production inhibition assay. Food Chem. 2013;141(3):1614–1618.
   PubMed Web of Science ®Google Scholar
• Yun BS, Kang HC, Koshino H, et al. Suillusin, a Unique Benzofuran from the Mushroom Suillus g ranulatus. J Nat Prod. 2001;64(9):1230–1231.
   PubMed Web of Science ®Google Scholar
• Yang Y, Gong T, Liu C, et al. Four new 2-arylbenzofuran derivatives from leaves of Morus alba L. Chem Pharm Bull. 2010;58(2):257–260.
   PubMed Web of Science ®Google Scholar
• Naik R, Harmalkar DS, Xu X, et al. Bioactive benzofuran derivatives: moracins A–Z in medicinal chemistry. Eur J Med Chem. 2015;90:379–393.
   PubMed Web of Science ®Google Scholar
• Wang XL, Di S XX, Shen T, et al. New phenolic compounds from the leaves of Artocarpus heterophyllus. Chin Chem Lett. 2017;28(1):37–40.
   Web of Science ®Google Scholar
• Wang Z, Wang Y, Wang B, et al. Design, synthesis, and evaluation of orally available clioquinol-moracin M hybrids as multitarget-directed ligands for cognitive improvement in a rat model of neurodegeneration in Alzheimer’s disease. J Med Chem. 2015;58(21):8616–8637.
   PubMed Web of Science ®Google Scholar
• Kyekyeku JO, Kusari S, Adosraku RK, et al. Prenylated 2-arylbenzofuran derivatives with potent antioxidant properties from Chlorophora regia (Moraceae). Fitoterapia. 2016;108:41–47.
   PubMed Web of Science ®Google Scholar
• Tan YX, Wang HQ, Chen RY. Anti-inflammatory and cytotoxic 2-arylbenzofurans from Morus wittiorum. Fitoterapia. 2012;83(4):750–753.
   PubMed Web of Science ®Google Scholar
• Kenchappa R, Bodke YD, Telkar S, et al. Antifungal and anthelmintic activity of novel benzofuran derivatives containing thiazolo benzimidazole nucleus: an in vitro evaluation. J Chem Biol. 2017;10(1):11–23.
   PubMedGoogle Scholar
• Liang Z, Xu H, Tian Y, et al. Design, synthesis and antifungal activity of novel benzofuran-triazole hybrids. Molecules. 2016;21(6):732–742.
   PubMed Web of Science ®Google Scholar
• Abdelhafez OM, Amin KM, Ali HI, et al. Design, synthesis and anticancer activity of benzofuran derivatives targeting VEGFR-2 tyrosine kinase. RSC Adv. 2014;4(23):1569–11579.
   Web of Science ®Google Scholar
• Dawood KM. Benzofuran derivatives: a patent review. Expert Opin Therap Pat. 2013;23(9):1133–1156.
   PubMed Web of Science ®Google Scholar
• Dawood KM. An update on benzofuran inhibitors: a patent review. Expert Opin Therap Pat. 2019;29(11):841–870.
   PubMed Web of Science ®Google Scholar
• Dawood KM, Farag AM, Abdel-Aziz HA. Synthesis and Antimicrobial Evaluation of Some 1,2,4-Triazole,1,3,4-Oxa(Thia)diazole and 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazine Derivatives. Heteroatom Chem. 2005;16(7):621–627.
   Web of Science ®Google Scholar
• Abdel-Aziz HA, Mekawey AAI, Dawood KM. Convenient Synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur J Med Chem. 2009;44(9):3637–3644.
   PubMed Web of Science ®Google Scholar
• Dawood KM, Abu-Deif HK. Synthesis and Antimicrobial Activity of Some New 1,2-Bis-[1,3-thiazolidin-3-yl]ethane Derivatives. Eur J Chem. 2013;4(3):277–284.
   Google Scholar
• Dawood KM, Abu-Deif HK. Synthesis and Antimicrobial Evaluation of Some New 1,2-Bis-(2-(N-arylimino)-1,3-thiazolidin-3-yl)ethane Derivatives. Chem Pharm Bull. 2014;62(5):439–445.
   PubMed Web of Science ®Google Scholar
• Dawood KM. Synthesis of spiro-pyrazole-3,3`-thiopyrano[2,3-b]pyridines and azolo[a]pyrido[2’,3’:5,6]-thiopyrano[3,4-d]pyrimidines as new ring systems with antifungal and antibacterial activities. J Heterocycl Chem. 2005;42(2):221–225.
   Web of Science ®Google Scholar
• Kassab RM, Khalil FS, Abbas AA. Synthesis and antimicrobial activities of some new bis (Schiff bases) and their triazole-based lariat macrocycles. Polycycl Aromat Compd. 2022;42(5):2751–2766.
   Web of Science ®Google Scholar
• Mahmoud HK, Abbas AA, Gomha SM. Synthesis, Antimicrobial Evaluation and Molecular Docking of New Functionalized Bis (1,3,4-Thiadiazole) and Bis (Thiazole) Derivatives. Polycycl Aromat Compd. 2021;41(9):2029–2041.
   Web of Science ®Google Scholar
• Mahmoud NF, Abbas AA, Mohamed GG. Synthesis,characterization,antimicrobial, and MOE evaluation of nano 1,2,4-triazole-based Schiff base ligand with some d-block metal ions. Appl Organomet Chem. 2021;35(6):e6219.
   Web of Science ®Google Scholar
• Sanad SM, Hanna DH, Mekky AE. Regioselective synthesis of novel antibacterial pyrazole-benzofuran hybrids: 2D NMR spectroscopy studies and molecular docking. J Mol Struct. 2019;1188:214–226.
   Web of Science ®Google Scholar
• Ashok D, Nalaparju N, Ram RM, et al. Microwave assisted synthesis of substituted (E)-{3-[2-(1,3-diphenyl-1H-pyrazol-4-yL)vinyl]benzofuran-2-yL}(phenyl)methanone and their antimicrobial activity. Res J Chem Environ. 2021;25(5):144–150.
   Google Scholar
• Elsherif MA, Hassan AS, Moustafa GO, et al. Antimicrobial evaluation and molecular properties prediction of pyrazolines incorporating benzofuran and pyrazole moieties. J Appl Pharm Sci. 2020;10(2):37–43.
   Google Scholar
• Idrees M, Kola S, Siddiqui NJ. An efficient synthesis of some novel bioactive azetidinone derivatives including 5-(benzofuran-2-yl) and 1-phenyl-1H-pyrazole-3-carboxamide moiety. Int J Pharm Sci Res. 2019;10(3):1214–1222.
   Web of Science ®Google Scholar
• Idrees M, Bodkhe YG, Siddiqui NJ, et al. Synthesis, Characterization and in vitro Antimicrobial Screening of Some Novel Series of 2-Azetidinone Derivatives Integrated with Quinoline, Pyrazole and Benzofuran Moieties. Asian J Chem. 2020;32(4):896–900.
   Google Scholar
• Idrees M, Kola S, Siddiqui NJ. Synthesis, characterization and antimicrobial screening of some novel 5-(benzofuran-2-yl)-n’-(2-substituted-4-oxothiazolidin-3-yl)-1-phenyl-1h-pyrazole-3-carboxamide derivatives. Rasayan J Chem. 2019;12(4):1725–1733.
   Google Scholar
• Mekky AE, Sanad SM. Novel bis (pyrazole-benzofuran) hybrids possessing piperazine linker: synthesis of potent bacterial biofilm and MurB inhibitors. Bioorg Chem. 2020;102:104094.
   PubMed Web of Science ®Google Scholar
• Li Y, Xu Q, Li Z, et al. Application of 2,4-bis (halomethyl) quinoline: synthesis and biological activities of 2,4-bis(benzofuran-2-yl)-and 2,4-bis(aroxymethyl) quinolines. Mol Divers. 2020;24(1):167–178.
   PubMed Web of Science ®Google Scholar
• Kumar G, Saroha B, Kumar R, et al. Design, synthesis, biological evaluation, and molecular docking studies of some novel N,N-dimethylaminopropoxy-substituted aurones. J Heterocycl Chem. 2022;59(2):297–308.
   Web of Science ®Google Scholar
• Abedinifar F, Farnia SMF, Hosseinihashemi SK, et al. Design and synthesis of new benzofuran-1,2,3-triazole hybrid preservatives and the evaluation of their antifungal potential against white and brown-rot fungi. BioResources. 2020;15(4):7828.
   Web of Science ®Google Scholar
• Sanjeeva P, Rao BS, Prasad VK, et al. Synthesis, Characterization and Antimicrobial Activities of 1-((5-Bromobenzofuran-2yl)methyl)-4-substituted phenyl-1H-1,2,3-triazoles. Asian J Chem. 2021;33(3):565–569.
   Google Scholar
• Vani I, Sireesha R, Mak KK, et al. Microwave assisted synthesis and antimicrobial and antioxidant activities of dimers of 1,2,3-triazole-benzofuran bearing alkyl spacer derivatives. Chem. Data Coll. 2021;31. 100605.
   Google Scholar
• Yadav JS, Bhaskar K. Synthesis and biological evaluation of a series of novel benzofuran-2-carboxylate 1, 2, 3-triazoles. Indian J Chem-Sect B. 2021;60(5):767–774.
   Web of Science ®Google Scholar
• Kumari HMN, Mathada MH, Hugar S, et al. Synthesis, Characterization and Antimicrobial Screening of 5-Bromo-Benzofuranyl Aryl Triazoles. J Appl Chem. 2019;8(4):1704–1710.
   Google Scholar
• Faiz S, Zahoor AF, Ajmal M, et al. Design, synthesis, antimicrobial evaluation, and laccase catalysis effect of novel benzofuran-oxadiazole and benzofuran-triazole hybrids. J Heterocycl Chem. 2019;56(10):2839–2852.
   Web of Science ®Google Scholar
• Hosseinihashemi SK, Toolabi M, Abedinifar F, et al. Synthesis and activity evaluation of new benzofuran-1,3,4-oxadiazole hybrids against wood-degrading fungi. BioResources. 2020;15(1):1085–1097.
   Web of Science ®Google Scholar
• Sanjeeva P, Subba Rao B, Kamala Prasad V, et al. Benzofuran-oxadiazole hybrids: design, Synthesis and antimicrobial activity studies. Res J Chem Environ. 2021;25(9):15–21.
   Google Scholar
• Idrees M, Kola SS, Siddiqui NJ. Facile synthesis, characterization and antimicrobial activities of novel 6-amino triazolo-thiadiazoles integrated with benzofuran and pyrazole moieties. Orient J Chem. 2019;35(6):1712–1717.
   Web of Science ®Google Scholar
• Kumari HMN, Mathada MH, Basavaraja KM. Synthesis, characterization and antimicrobial activity of benzofuran derivatives. J Appl Chem. 2021;10(4):438–444.
   Google Scholar
• Kumar AK, Sunitha V, Shankaraiah P, et al. Synthesis, characterization and antimicrobial evaluation of some novel (3-methyl-5-((3-phenylisoxazol-5-yl)methoxy)benzofuran-2-yl)(phenyl) methanones. Indian J Chem-Sect B. 2021;60(8):1137–1141
   Google Scholar
• El-Khouly OA, Henen MA, Magda AA, et al. Synthesis, anticancer and antimicrobial evaluation of new benzofuran based derivatives: PI3K inhibition, quorum sensing and molecular modeling study. Bioorg Med Chem. 2021;31:115976.
   PubMed Web of Science ®Google Scholar
• Kumar M, Basavaraja KM, Mathada MH, et al. Novel synthesis and biological activity of (2E)-1-(3-amino-5-chloro-1-benzofuran-2-yl)-3-arylprop-2-en-1-ones and their derivatives. Rasayan J Chem. 2021;14(3):1699–1710.
   Google Scholar
• Catinella G, Mattio LM, Musso L, et al. Structural requirements of benzofuran derivatives dehydro-d-and dehydro-e-viniferin for antimicrobial activity against the foodborne pathogen Listeria monocytogenes. Internat J Mol Sci. 2020;21(6):2168.
   PubMed Web of Science ®Google Scholar
• Kumari HMN, Mathada MH, Basavaraja KM. Synthesis, Characterization, Biological Activity of 5-Bromo-benzofuran-2-carboxylic acid (Substituted-benzylidene)-hydrazides and their Derivatives. J Applicable Chem. 2020;9:223–228.
   Google Scholar
• Mathada MH, Kumari HMN, Kumar KM, et al. Synthesis, Characterization and Biological Activity of Various3-(Substituted-Benzyl)-5-(5-Bromo-7-Methoxy-Benzofuran-2-yl)-3H-[1,3,4]Oxadiazole-2-Thiones. J Applicable Chem. 2019;8(2):574–580
   Google Scholar
• Gao F, Wang T, Gao M, et al. Benzofuran-isatin-imine hybrids tethered via different length alkyl linkers: design, synthesis and in vitro evaluation of anti-tubercular and anti-bacterial activities as well as cytotoxicity. Eur J Med Chem. 2019;165:323–331.
   PubMed Web of Science ®Google Scholar
• Mathada MH, Naveenakumari HM, Basavaraja KM. Synthesis, characterization, antibacterial and antifungal screening of various 5-Bromo-7-methoxy-benzofuran schiff bases. J Applicable Chem. 2019;8(1):165–170.
   Google Scholar
• Hanumanagouda H, Mathada MH, Basavaraja KM. Curtius rearrangement reactions using 7-methoxybenzofuran-2-carbonylazide. J Appl Chem. 2022;11(3):356–367.
   Google Scholar
• Li M, Ye Y, He L, et al. Domino Cyclization/ Trifluoromethylation of 2-Alknylphenols for the Synthesis of 3-(Trifluoromethyl) benzofurans and evaluation of their antibacterial and antifungal activities. Asian J Org Chem. 2019;8(5):702–709.
   Web of Science ®Google Scholar
• Lei S, Hu Y, Yuan C, et al. Discovery of Sortase A covalent inhibitors with benzofuranene cyanide structures as potential antibacterial agents against Staphylococcus aureus. Eur J Med Chem. 2022;229:114032.
   PubMed Web of Science ®Google Scholar
• Kundlikar SG, Randhavane PV, Akolkar HN, et al. Synthesis, characterization and antibacterial screening of fluorinated benzofuran containing heterocycles. Indian J Chem, Section B. 2019;58B(4):504–510
   Google Scholar
• Xu H, Hou Z, Liang Z, et al. Design, synthesis and antifungal activity of benzofuran and its analogues. Chin J Chem. 2019;37(12):1245–1250.
   Web of Science ®Google Scholar
• Liu HX, Ji F, Chen Y, et al. De novo and divergent synthesis of highly functionalized furans by cascade reactions of 2-Hydroxy-1,4-diones with Nucleophiles. Chem Eur J. 2021;27(16):5225–5229.
   PubMed Web of Science ®Google Scholar
• Pagano C, Ceccarini MR, Calarco P, et al. Bioadhesive polymeric films based on usnic acid for burn wound treatment: antibacterial and cytotoxicity studies. Colloids Surf B: Biointerfaces. 2019;178:488–499.
   PubMed Web of Science ®Google Scholar
• Francolini I, Giansanti L, Piozzi A, et al. Glucosylated liposomes as drug delivery systems of usnic acid to address bacterial infections. Colloids Surf B: Biointerfaces. 2019;181:632–638.
   PubMed Web of Science ®Google Scholar
• Battista S, Bellio P, Celenza G, et al. Correlation of physicochemical and antimicrobial properties of liposomes loaded with (+)-Usnic Acid. Chem Plus Chem. 2020;85(5):1014–1021.
   Google Scholar
• Rauschenbach M, Lawrenson SB, Taresco V, et al. Antimicrobial hyperbranched polymer-usnic acid complexes through a combined ROP-RAFT strategy. Macromol Rapid Commun. 2020;41(18):2000190.
   Web of Science ®Google Scholar
• Dharavath R, Sarasija M, Ram Reddy M, et al. Microwave-assisted synthesis and evaluation of their antiproliferative, antimicrobial, activities and DNA Binding studies of (3-Methyl-7H-furo [2,3-f] chromen-2-yl)(aryl)methanones. Med Chem Res. 2022;31(6):993–1002.
   Web of Science ®Google Scholar
• Zaher AM, Sultan R, Ramadan T, et al. New antimicrobial and cytotoxic benzofuran glucoside from Senecio glaucus L. Nat Prod Res. 2021;36(1):136–141.
   Web of Science ®Google Scholar
• Li HL, Li XM, Yang SQ, et al. Prenylated phenol and benzofuran derivatives from Aspergillus terreus EN-539, an endophytic fungus derived from marine red alga Laurencia okamurai. Mar Drugs. 2019;17(11):605.
   PubMed Web of Science ®Google Scholar
• Lin S, Liu RH, Ma GQ, et al. Two new compounds from the heartwood of Dalbergia melanoxylon. Nat Prod Res. 2020;34(19):2794–2801.
   PubMed Web of Science ®Google Scholar
• Iyun O, Ahmed J, Muhammad SS, et al. GC-MS Analysis of Methanol Extract of Strychnos Innocua (Delile) Root Bark. Adv J Chem. Section A. 2022;5(2):104–117
   Google Scholar
• Chao R, Said G, Zhang Q, et al. Design, semisynthesis, insecticidal and antibacterial activities of a series of marine-derived geodin derivatives and their preliminary structure-activity relationships. Mar Drugs. 2022;20(2):82.
   PubMed Web of Science ®Google Scholar
• Wu YL, Wei J, Meng YF, et al. Synthesis, Antifungal activity, and QSAR studies of benzbutyrolactone derivatives based on a-methylene-?-butyrolactone Scaffold. Russ J Gen Chem. 2022;92(6):1085–1097.
   Web of Science ®Google Scholar
• Robin M, Maresca M, Olleik H, et al. Synthesis of Aurone phytoprotectives, decontaminats and disinfectant agents for controlling bacteria and/or fungi. PCT Int. Appl. 2022;WO2022008678.
   Google Scholar
• Hou X, Li Y, Aisa HA. Diastereoselective preparation of hetero- 1135 cyclic aurone derivatives and their antibacterial activity. PCT Int. Appl. 2022;CN114349743A.
   Google Scholar