Brønsted acid functionalized carbon catalyst for synthesis of biologically active coumarin-substituted bis(indolyl)methanes

Sravanthi, 2016, Indoles — A promising scaffold for drug development, Eur. J. Pharm. Sci., 91, 1, 10.1016/j.ejps.2016.05.025 Shiri, 2010, Bis- and Trisindolylmethanes (BIMs and TIMs) †, Chem. Rev., 110, 2250, 10.1021/cr900195a Bell, Ronit, S. Carmeli, N. Sar, Vibrindole A, a Metabolite of the Marine Bacterium, Vibrio parahaemolyticus, Isolated from the Toxic Mucus of the Boxfish Ostracioncubicus, J. Natural Products. 57 (11) (1994) 1587-1590. 10.1021/np50113a022. Sujatha, 2009, Synthesis, analgesic and anti-inflammatory activities of bis(indolyl)methanes, Indian J. Chem., 48, 267 Taha, 2018, Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies, Eur. J. Med. Chem., 143, 1757, 10.1016/j.ejmech.2017.10.071 Marrelli, 2013, Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells, Nat. Prod. Res., 27, 2039, 10.1080/14786419.2013.824440 Dasbasi, 2011, Indium triflate-catalyzed coupling of indoles with acyl phosphonates: synthesis of bis(indolyl)methane phosphonates, Tetrahedron, 67, 3355, 10.1016/j.tet.2011.03.061 Xiao, 2016, Catalyst-free dehydrative S N 1-type reaction of indolyl alcohols with diverse nucleophiles “on water”, Green Chem., 18, 1032, 10.1039/C5GC01838B Qiang, Wenwen, X. Liu, T.P. Loh, Supported Iridium Catalyst for the Green Synthesis of 3,3′-Bis(indolyl)methanes Using Methanol As the Bridging Methylene Source, ACS Sustainable Chemistry & Engineering. 7 (9) (2019) 8429-8439. https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.9b00094. Ling, 2019, Ga(OTf) 3 -Catalyzed Temperature-Controlled Regioselective Friedel–Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3′-and 3,6′-Bis(indolyl)methanes, Org. Lett., 21, 3396, 10.1021/acs.orglett.9b01135 Qu, 2019, A coumarin-based fluorescent probe for ratiometric detection of hydrazine and its application in living cells, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 210, 381, 10.1016/j.saa.2018.11.007 Li, 2018, Coumarin-Based Oxime Esters: Photobleachable and Versatile Unimolecular Initiators for Acrylate and Thiol-Based Click Photopolymerization under Visible Light-Emitting Diode Light Irradiation, ACS Appl. Mater. Interfaces, 10, 16113, 10.1021/acsami.8b01767 Hu, 2017, Recent developments of coumarin-containing derivatives and their anti-tubercular activity, Eur. J. Med. Chem., 136, 122, 10.1016/j.ejmech.2017.05.004 Fan, 2018, Coumarin-triazole Hybrids and Their Biological Activities: Coumarin-triazole Hybrids, J. Heterocyclic Chem., 55, 791, 10.1002/jhet.3112 Noroozizadeh, 2018, Synthesis of bis-coumarins over acetic acid functionalized poly(4-vinylpyridinum) bromide (APVPB) as a green and efficient catalyst under solvent-free conditions and their biological activity, J. IRAN Chem. Soc., 15, 471, 10.1007/s13738-017-1247-1 Singh, 2020, Recent Developments on the Synthesis of Biologically Significant bis/tris(indolyl)methanes under Various Reaction Conditions: A Review, COC, 24, 583, 10.2174/1385272824666200228092752 Xu, 2017, Isatin hybrids and their anti-tuberculosis activity, Chin. Chem. Lett., 28, 159, 10.1016/j.cclet.2016.07.032 Tan, 2011, Brønsted acid catalyzed Diels–Alder reactions of 2-vinylindoles and 3-nitrocoumarins: an expedient synthesis of coumarin-fused tetrahydrocarbazoles, Tetrahedron, 67, 446, 10.1016/j.tet.2010.11.019 Kumar, 2018, Coumarin Derivatives as Anticancer Agents for Lung Cancer Therapy: A Review, ACAMC, 18, 964, 10.2174/1871520618666171229185926 Yuan, 2019, A consecutive one-pot two-step approach to novel trifluoromethyl-substituted bis(indolyl)methane derivatives promoted by Sc(OTf)3 and p-TSA, Tetrahedron Lett., 60, 151329, 10.1016/j.tetlet.2019.151329 Wang, 2016, A FeCl 3 -catalyzed highly regioselective 1,2-addition/substitution sequence for the construction of coumarin-substituted bis(indolyl)methanes, Org. Biomol. Chem., 14, 4420, 10.1039/C6OB00515B Hara, 2004, A Carbon Material as a Strong Protonic Acid, Angew. Chem., 116, 3015, 10.1002/ange.200453947 Nakajima, 2012, Amorphous Carbon with SO 3 H Groups as a Solid Brønsted Acid Catalyst, ACS Catal., 2, 1296, 10.1021/cs300103k Gupta, 2014, Oxidative transformation of alcohols and organic halides in aqueous solution, New J. Chem., 38, 3749, 10.1039/C4NJ00393D Konwar, 2019, Pekka, SO3H-Containing Functional Carbon Materials: Synthesis, Structure, and Acid Catalysis, Chem. Rev., 119, 11576, 10.1021/acs.chemrev.9b00199 Kalla, 2018, Synthesis of Bis(indolyl)methanes Using Hyper-Cross-Linked Polyaromatic Spheres Decorated with Bromomethyl Groups as Efficient and Recyclable Catalysts, ACS Omega, 3, 2242, 10.1021/acsomega.7b01925 Ding, 2015, Heterogenization of homogenous reaction system on carbon surface with ionic liquid as mediator, Green Chem., 17, 1107, 10.1039/C4GC01814A Gupta, 2019, Valorisation of Biomass Derived Furfural and Levulinic Acid by Highly Efficient Pd@ND Catalyst, Energy Technol., 7, 269, 10.1002/ente.201800524 Ding, 2015, Entrapping an Ionic Liquid with Nanocarbon: The Formation of a Tailorable and Functional Surface, Angew. Chem., 127, 233, 10.1002/ange.201408201 Damlin, 2015, Non-covalent modification of graphene sheets in PEDOT composite materials by ionic liquids, Carbon, 93, 533, 10.1016/j.carbon.2015.05.055 Dogra, 2021, Metal‐Free g‐C 3 N 4 /Graphite Composite Based Carbocatalyst for Epoxidation of Styrene, ChemistrySelect, 6, 7118, 10.1002/slct.202101542 Choi, 2013, Additional doping of phosphorus and/or sulfur into nitrogen-doped carbon for efficient oxygen reduction reaction in acidic media, Phys. Chem. Chem. Phys., 15, 1802, 10.1039/C2CP44147K Tanabe, 1992, On the characterization of graphite, J. Nucl. Mater., 191-194, 330, 10.1016/0022-3115(92)90780-O Kaur, 2019, Indole hybridized diazenyl derivatives: synthesis, antimicrobial activity, cytotoxicity evaluation and docking studies, BMC Chemistry, 13, 10.1186/s13065-019-0580-0 Chaturvedi, 2001, Prediction of pharmacokinetic properties using experimental approaches during early drug discovery, Curr. Opin. Chem. Biol., 5, 452, 10.1016/S1367-5931(00)00228-3 Singhal, 2019, Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole, Heliyon, 5, e02596, 10.1016/j.heliyon.2019.e02596 Han, 2019, In silico ADME and Toxicity Prediction of Ceftazidime and Its Impurities, Front. Pharmacol., 10, 434, 10.3389/fphar.2019.00434 Hamza, 2019, Design and Synthesis of Novel Inhibitor against Ser121 and Val122 Mutations in P53 Cancer Gene, app, 7, 63, 10.13189/app.2019.070402 Kamath, 2015, Some new indole–coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies, Bioorg. Chem., 63, 101, 10.1016/j.bioorg.2015.10.001 Kamath, 2017, Indole-coumarin-thiadiazole hybrids: An appraisal of their MCF-7 cell growth inhibition, apoptotic, antimetastatic and computational Bcl-2 binding potential, Eur. J. Med. Chem., 136, 442, 10.1016/j.ejmech.2017.05.032