{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,12]],"date-time":"2025-12-12T13:39:08Z","timestamp":1765546748748,"version":"build-2065373602"},"reference-count":92,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2021,4,11]],"date-time":"2021-04-11T00:00:00Z","timestamp":1618099200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Researchers supporting project number, King Saud University","award":["RSP-2020\/222"],"award-info":[{"award-number":["RSP-2020\/222"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A simple and efficient BF3-OEt2 promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, 3w, having N,N-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC50 value 0.02 \u00b5M and 0.8 \u00b5M against HT-29 and Hepg2 cell lines, respectively, and compound 3i was most active amongst the series with IC50 value 1.5 \u00b5M against A549 cells. Molecular docking study and mechanism of reaction have briefly beendiscussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles.<\/jats:p>","DOI":"10.3390\/molecules26082202","type":"journal-article","created":{"date-parts":[[2021,4,12]],"date-time":"2021-04-12T05:52:00Z","timestamp":1618206720000},"page":"2202","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8977-0367","authenticated-orcid":false,"given":"Iqbal N.","family":"Shaikh","sequence":"first","affiliation":[{"name":"Department of Chemistry, Poona College of Arts, Science and Commerce, Camp, Pune 411 001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Abdul","family":"Rahim","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Poona College of Arts, Science and Commerce, Camp, Pune 411 001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shaikh","family":"Faazil","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Poona College of Arts, Science and Commerce, Camp, Pune 411 001, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2768-1235","authenticated-orcid":false,"given":"Syed Farooq","family":"Adil","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mohamed E.","family":"Assal","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mohammad Rafe","family":"Hatshan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,4,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"160","DOI":"10.2174\/1871520615666150520144217","article-title":"Indole Derivatives as Anticancer Agents for Breast Cancer Therapy: A Review","volume":"16","author":"Sidhu","year":"2015","journal-title":"Anti-Cancer Agents Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1007\/s00044-017-2065-9","article-title":"Novel indole derivatives as potential anticancer agents: Design, synthesis and biological screening","volume":"27","author":"Prakash","year":"2018","journal-title":"Med. Chem. Res."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Mor, M., Spadoni, G., Diamantini, G., Bedini, A., Tarzia, G., Silva, C., Vacondio, F., Rivara, M., Plazzi, P.V., and Franceschinit, D. (2003). Antioxidant and cytoprotective activity of indole derivatives related to melatonin. Developments in Tryptophan and Serotonin Metabolism, Springer.","DOI":"10.1007\/978-1-4615-0135-0_65"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1143","DOI":"10.3109\/14756366.2012.717223","article-title":"Antioxidant activity of indole-based melatonin analogues in erythrocytes and their voltammetric characterization","volume":"28","author":"Suzen","year":"2013","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"58","DOI":"10.3109\/14756366.2011.631183","article-title":"Synthesis of new indole-2-carboxamide and 3-acetamide derivatives and evaluation their antioxidant properties","volume":"28","author":"Bakar","year":"2013","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"554","DOI":"10.1093\/rheumatology\/34.6.554","article-title":"A comparative study of tenidap, a cytokine-modulating anti-rheumatic drug, and diclofenac in rheumatoid arthritis: A 24-week analysis of a 1-year clinical trial","volume":"34","author":"Wylie","year":"1995","journal-title":"Rheumatology"},{"key":"ref_7","first-page":"622","article-title":"Drug therapy reviews: Antirheumatic agents","volume":"36","author":"Evens","year":"1979","journal-title":"Am. J. Hosp. Pharm."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3172","DOI":"10.1021\/jm0512490","article-title":"Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide","volume":"49","author":"Ragno","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2120","DOI":"10.2174\/138161209788489168","article-title":"Developments of indoles as anti-HIV-1 inhibitors","volume":"15","author":"Xu","year":"2009","journal-title":"Curr. Pharm. Des."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1700","DOI":"10.2174\/13895575113139990075","article-title":"Recent development of new substituted indole and azaindole derivatives as anti-HIV agents","volume":"13","author":"Olgen","year":"2013","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1016\/j.ejmech.2005.10.006","article-title":"3-Bromo-4-(1H-3-indolyl)-2, 5-dihydro-1H-2, 5-pyrroledione derivatives as new lead compounds for antibacterially active substances","volume":"41","author":"Mahboobi","year":"2006","journal-title":"Eur. J. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"282","DOI":"10.1016\/j.ejmech.2007.03.026","article-title":"Synthesis, in vitro antiproliferative activities, and Chk1 inhibitory properties of pyrrolo [3, 4-a] carbazole-1, 3-diones, pyrrolo [3, 4-c] carbazole-1, 3-diones, and 2-aminopyridazino [3, 4-a] pyrrolo [3, 4-c] carbazole-1, 3, 4, 7-tetraone","volume":"43","author":"Conchon","year":"2008","journal-title":"Eur. J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6785","DOI":"10.1016\/j.bmc.2010.07.045","article-title":"Novel indolylmaleimide acts as GSK-3\u03b2 inhibitor in human neural progenitor cells","volume":"18","author":"Karapetyan","year":"2010","journal-title":"Biorg. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"519","DOI":"10.1007\/s12272-011-0401-z","article-title":"Synthesis and cytotoxicity of novel 3-amino-4-indolylmaleimide derivatives","volume":"34","author":"Zhao","year":"2011","journal-title":"Arch. Pharmacal. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"7549","DOI":"10.1021\/jm0609871","article-title":"Profile and Molecular Modeling of 3-(Indole-3-yl)-4-(3, 4, 5-trimethoxyphenyl)-1 H-pyrrole-2, 5dione (1) as a Highly Selective VEGF-R2\/3 Inhibitor","volume":"49","author":"Peifer","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"604","DOI":"10.1016\/j.orgel.2009.12.025","article-title":"Asymmetric indolylmaleimides as non-dopant type red color emitting dyes","volume":"11","author":"Lee","year":"2010","journal-title":"Org. Electron."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1039\/b719160j","article-title":"Efficient palladium-catalyzed synthesis of 3-aryl-4-indolylmaleimides","volume":"6","author":"Tillack","year":"2008","journal-title":"Org. Biomol. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3583","DOI":"10.1021\/ol701431g","article-title":"Bisindolylmaleimides with large stokes shift and long-lasting chemiluminescence properties","volume":"9","author":"Nakazono","year":"2007","journal-title":"Org. Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/j.ejmech.2017.04.003","article-title":"Indoles as therapeutics of interest in medicinal chemistry: Bird\u2019s eye view","volume":"134","author":"Chadha","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ejps.2016.05.025","article-title":"Indoles\u2014a promising scaffold for drug development","volume":"91","author":"Sravanthi","year":"2016","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4489","DOI":"10.1021\/cr900211p","article-title":"Marine indole alkaloids: Potential new drug leads for the control of depression and anxiety","volume":"110","author":"Hamann","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"543","DOI":"10.1055\/s-0035-1545845","article-title":"Bioactive natural products against prostate cancer: Mechanism of action and autophagic\/apoptotic molecular pathways","volume":"81","author":"Gioti","year":"2015","journal-title":"Planta Med."},{"key":"ref_23","first-page":"1002","article-title":"Targeted regulation of PI3K\/Akt\/mTOR\/NF-\u03baB signaling by indole compounds and their derivatives: Mechanistic details and biological implications for cancer therapy","volume":"13","author":"Ahmad","year":"2013","journal-title":"Anti-Cancer Agents Med. Chem. Former. Curr. Med. Chem. Anti Cancer Agents"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1124\/mol.109.058180","article-title":"Targeting of the Akt-nuclear factor-\u03baB signaling network by [1-(4-chloro-3-nitrobenzenesulfonyl)-1H-indol-3-yl]-methanol (OSU-A9), a novel indole-3-carbinol derivative, in a mouse model of hepatocellular carcinoma","volume":"76","author":"Omar","year":"2009","journal-title":"Mol. Pharmacol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"8899","DOI":"10.1007\/s11033-012-1757-y","article-title":"N-(1-Pyrenyl) maleimide inhibits telomerase activity in a cell free system and induces apoptosis in Jurkat cells","volume":"39","author":"Huang","year":"2012","journal-title":"Mol. Biol. Rep."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"25831","DOI":"10.3390\/ijms161025831","article-title":"Site-specific PEGylation of therapeutic proteins","volume":"16","author":"Dozier","year":"2015","journal-title":"Int. J. Mol. Sci."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1021\/bc1004685","article-title":"In situ maleimide bridging of disulfides and a new approach to protein PEGylation","volume":"22","author":"Schumacher","year":"2011","journal-title":"Bioconjugate Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"24828","DOI":"10.1039\/C7RA04606E","article-title":"Use of a next generation maleimide in combination with THIOMAB\u2122 antibody technology delivers a highly stable, potent and near homogeneous THIOMAB\u2122 antibody-drug conjugate (TDC)","volume":"7","author":"Nunes","year":"2017","journal-title":"RSC Adv."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2387","DOI":"10.1039\/C6SC05149A","article-title":"Development of a facile antibody\u2013drug conjugate platform for increased stability and homogeneity","volume":"8","author":"Gupta","year":"2017","journal-title":"Chem. Sci."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Yao, H., Jiang, F., Lu, A., and Zhang, G. (2016). Methods to design and synthesize antibody-drug conjugates (ADCs). Int. J. Mol. Sci., 17.","DOI":"10.3390\/ijms17020194"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1475","DOI":"10.1039\/C1CC14713G","article-title":"Maleimide-functionalised organoruthenium anticancer agents and their binding to thiol-containing biomolecules","volume":"48","author":"Hanif","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2249","DOI":"10.1039\/c3cc39258a","article-title":"Maleimide-functionalised platinum (IV) complexes as a synthetic platform for targeted drug delivery","volume":"49","author":"Pichler","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2224","DOI":"10.1038\/bjc.2014.164","article-title":"Small molecule MIRA-1 induces in vitro and in vivo anti-myeloma activity and synergizes with current anti-myeloma agents","volume":"110","author":"Saha","year":"2014","journal-title":"Br. J. Cancer"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"30384","DOI":"10.1074\/jbc.M501664200","article-title":"Reactivation of mutant p53 and induction of apoptosis in human tumor cells by maleimide analogs","volume":"280","author":"Bykov","year":"2005","journal-title":"J. Biol. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"324","DOI":"10.1021\/jm00177a024","article-title":"Synthesis and anticancer activity of nitrosourea derivatives of phensuximide","volume":"23","author":"Crider","year":"1980","journal-title":"J. Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"5577","DOI":"10.1016\/j.tet.2005.03.099","article-title":"Hirsutellones A\u2013E, antimycobacterial alkaloids from the insect pathogenic fungus Hirsutella nivea BCC 2594","volume":"61","author":"Isaka","year":"2005","journal-title":"Tetrahedron"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6954","DOI":"10.1016\/j.bmc.2006.06.043","article-title":"Cytotoxic labdane alkaloids from an ascidian Lissoclinum sp.: Isolation, structure elucidation, and structure\u2013activity relationship","volume":"14","author":"Uddin","year":"2006","journal-title":"Biorg. Med. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1515\/hc-2013-0050","article-title":"Synthesis and biological activity of novel series of heterocyclic compounds containing succinimide moiety","volume":"19","author":"Kuran","year":"2013","journal-title":"Heterocycl. Commun."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.1016\/0040-4020(75)87076-1","article-title":"NaBH4 reduction of cyclic imides","volume":"31","author":"Hubert","year":"1975","journal-title":"Tetrahedron"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/S0040-4020(01)93601-4","article-title":"A regioselective reduction of gem-disubstituted succinimides","volume":"34","author":"Wijnberg","year":"1978","journal-title":"Tetrahedron"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4351","DOI":"10.1021\/jm800150d","article-title":"Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors","volume":"51","author":"Liou","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4941","DOI":"10.1021\/jm900060s","article-title":"Synthesis and evaluation of 3-aroylindoles as anticancer agents: Metabolite approach","volume":"52","author":"Wu","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"5229","DOI":"10.1016\/j.bmcl.2010.06.152","article-title":"Synthesis of 3, 3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity","volume":"20","author":"Kamal","year":"2010","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1111\/j.1747-0285.2011.01216.x","article-title":"Synthesis and comparison of antioxidant properties of indole-based melatonin analogue indole amino acid derivatives","volume":"79","author":"Suzen","year":"2012","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2873","DOI":"10.1021\/cr040639b","article-title":"Synthesis and functionalization of indoles through palladium-catalyzed reactions","volume":"105","author":"Cacchi","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3508","DOI":"10.1021\/cr2003954","article-title":"Indoles in multicomponent processes (MCPs)","volume":"112","author":"Shiri","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"9608","DOI":"10.1002\/anie.200901843","article-title":"Catalytic functionalization of indoles in a new dimension","volume":"48","author":"Bandini","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1665","DOI":"10.1021\/ol049498q","article-title":"Selective Functionalization in Positions 2 and 3 of Indole via an Iodine\u2212 Copper Exchange Reaction","volume":"6","author":"Yang","year":"2004","journal-title":"Org. Lett."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"3664","DOI":"10.1021\/acs.orglett.7b01681","article-title":"Regioselective direct C-4 functionalization of indole: Total syntheses of (\u2212)-agroclavine and (\u2212)-elymoclavine","volume":"19","author":"Lv","year":"2017","journal-title":"Org. Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"4956","DOI":"10.1021\/ol1020948","article-title":"Direct functionalization of indoles: Copper-catalyzed malonyl carbenoid insertions","volume":"12","author":"Johansen","year":"2010","journal-title":"Org. Lett."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1730","DOI":"10.3762\/bjoc.8.198","article-title":"Palladium-catalyzed dual C\u2013H or N\u2013H functionalization of unfunctionalized indole derivatives with alkenes and arenes","volume":"8","author":"Broggini","year":"2012","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"32559","DOI":"10.1039\/C7RA06004A","article-title":"Direct C-2 acylation of indoles with toluene derivatives via Pd (II)-catalyzed C\u2013H activation","volume":"7","author":"Zhao","year":"2017","journal-title":"RSC Adv."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.molcata.2016.07.042","article-title":"Direct CC coupling of indoles with alkylamides via oxidative CH functionalization using Fe3O (BDC) 3 as a productive heterogeneous catalyst","volume":"423","author":"Doan","year":"2016","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"10925","DOI":"10.1002\/chem.201702338","article-title":"Direct C2-Functionalization of Indoles Triggered by the Generation of Iminium Species from Indole and Sulfonium Salt","volume":"23","author":"Tayu","year":"2017","journal-title":"Chem. A Eur. J."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1021\/cr900184e","article-title":"Palladium-catalyzed ligand-directed C\u2212 H functionalization reactions","volume":"110","author":"Lyons","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1021\/ar200185g","article-title":"Weak coordination as a powerful means for developing broadly useful C\u2013H functionalization reactions","volume":"45","author":"Engle","year":"2012","journal-title":"Acc. Chem. Res."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1763","DOI":"10.1002\/anie.201107859","article-title":"A New Direction in C-H Alkenylation: Silanol as a Helping Hand","volume":"51","author":"Mewald","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"5879","DOI":"10.1021\/cr300153j","article-title":"Ruthenium (II)-catalyzed C\u2013H bond activation and functionalization","volume":"112","author":"Arockiam","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"3199","DOI":"10.1021\/ol048663z","article-title":"New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: Controlling the regioselectivity","volume":"6","author":"Bandini","year":"2004","journal-title":"Org. Lett."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"6314","DOI":"10.1021\/ja0608139","article-title":"Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1 H-indoles using trialkylboranes","volume":"128","author":"Trost","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"11418","DOI":"10.1021\/ja105111n","article-title":"Enantioselective construction of spiroindolenines by Ir-catalyzed allylic alkylation reactions","volume":"132","author":"Wu","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"4301","DOI":"10.1002\/ange.201209485","article-title":"Hydrogen-Bond-Promoted Palladium Catalysis: Allylic Alkylation of Indoles with Unsymmetrical 1, 3-Disubstituted Allyl Acetates Using Chiral Bis (sulfoxide) Phosphine Ligands","volume":"125","author":"Du","year":"2013","journal-title":"Angew. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"740","DOI":"10.1021\/ol3032736","article-title":"Pd-catalyzed asymmetric allylic alkylations of 3-substituted indoles using chiral P\/olefin ligands","volume":"15","author":"Liu","year":"2013","journal-title":"Org. Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1039\/C2SC21085A","article-title":"Diversity oriented synthesis of indole-based peri-annulated compounds via allylic alkylation reactions","volume":"4","author":"Xu","year":"2013","journal-title":"Chem. Sci."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"8044","DOI":"10.1039\/C6OB01523A","article-title":"Pd-catalyzed cascade allylic alkylation and dearomatization reactions of indoles with vinyloxirane","volume":"14","author":"Gao","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1016\/j.tetlet.2004.11.139","article-title":"First example of the C-alkylation of indoles with Baylis\u2013Hillman acetates","volume":"46","author":"Yadav","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2525","DOI":"10.1021\/ol070878w","article-title":"A Highly \u03b1-Regioselective AgOTf-Catalyzed Nucleophilic Substitution of the Baylis\u2212 Hillman Acetates with Indoles","volume":"9","author":"Shafiq","year":"2007","journal-title":"Org. Lett."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"8451","DOI":"10.1021\/jo301313m","article-title":"Synthesis of Indolylquinolines, Indolylacridines, and Indolylcyclopenta [b] quinolines from the Baylis\u2013Hillman Adducts: An in Situ [1, 3]-Sigmatropic Rearrangement of an Indole Nucleus To Access Indolylacridines and Indolylcyclopenta [b] quinolines","volume":"77","author":"Ramesh","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"438","DOI":"10.1021\/jo502443a","article-title":"Formation of Cyclohepta [b] indole Scaffolds via Heck Cyclization: A Strategy for Structural Analogues of Ervatamine Group of Indole Alkaloid","volume":"80","author":"Goswami","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"656","DOI":"10.1021\/ol1028964","article-title":"Regioselective alkylation of heteroaromatic compounds with 3-methyl-2-quinonyl boronic acids","volume":"13","author":"Veguillas","year":"2011","journal-title":"Org. Lett."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/j.tetlet.2011.11.007","article-title":"Highly stereoselective imidazolethiones mediated Friedel\u2013Crafts alkylation of indole derivatives","volume":"53","author":"Liang","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"3738","DOI":"10.1021\/ol401616a","article-title":"Catalytic Friedel\u2013Crafts Reaction of Aminocyclopropanes","volume":"15","author":"Loup","year":"2013","journal-title":"Org. Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"8869","DOI":"10.1039\/c3cc44828b","article-title":"Bis-cyclometallated gold (III) complexes as efficient catalysts for synthesis of propargylamines and alkylated indoles","volume":"49","author":"Ko","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"9227","DOI":"10.1021\/acs.joc.6b01805","article-title":"Synthesis of 3-Indolylglycine Derivatives via Dinuclear Zinc Catalytic Asymmetric Friedel\u2013Crafts Alkylation Reaction","volume":"81","author":"Wang","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1172","DOI":"10.1002\/cctc.201601583","article-title":"Friedel\u2013Crafts Alkylation of Indoles with Nitroalkenes through Hydrogen-Bond-Donating Metal\u2013Organic Framework","volume":"9","author":"Rao","year":"2017","journal-title":"ChemCatChem"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1055\/s-1997-1214","article-title":"A direct synthesis of 3-(pyrrolidin-3-yl) indoles for use as conformationally restricted analogs of tryptamines","volume":"1997","author":"Macor","year":"1997","journal-title":"Synthesis"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"2363","DOI":"10.1016\/S0040-4020(99)00029-0","article-title":"Synthesis of indolo [3, 2-a] pyrrolo [3, 4-c] carbazole in one step from indole and maleimide","volume":"55","author":"Bergman","year":"1999","journal-title":"Tetrahedron"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"2719","DOI":"10.1055\/s-0033-1339515","article-title":"Highly Efficient Aluminum Trichloride Catalyzed Michael Addition of Indoles and Pyrroles to Maleimides","volume":"45","author":"An","year":"2013","journal-title":"Synthesis"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1016\/j.arabjc.2013.04.009","article-title":"Convenient synthesis of substituted pyrroles via a cerium (IV) ammonium nitrate (CAN)-catalyzed Paal\u2013Knorr reaction","volume":"9","author":"Kamal","year":"2016","journal-title":"Arab. J. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"979","DOI":"10.1016\/j.jksus.2019.08.001","article-title":"Microwave-assisted green synthesis of 1, 5 benzodiazepines using Cu (II)-clay nanocatalyst","volume":"32","author":"Shaikh","year":"2020","journal-title":"J. King Saud Univ. Sci."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1039\/C7OB02241G","article-title":"Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline","volume":"16","author":"Rahim","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"11080","DOI":"10.1016\/j.tet.2013.11.017","article-title":"A convenient synthesis of bisamides with BF3 etherate as catalyst","volume":"69","author":"Zhang","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1080\/00397910903029842","article-title":"BF3\u00b7 OEt2: An Efficient Catalyst for Transesterification of \u03b2-Ketoesters","volume":"40","author":"Yang","year":"2010","journal-title":"Synth. Commun."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"9617","DOI":"10.1021\/acs.jmedchem.7b00974","article-title":"Discovery of a novel and selective indoleamine 2, 3-dioxygenase (IDO-1) inhibitor 3-(5-fluoro-1 H-indol-3-yl) pyrrolidine-2, 5-dione (EOS200271\/PF-06840003) and its characterization as a potential clinical candidate","volume":"60","author":"Crosignani","year":"2017","journal-title":"J. Med. Chem."},{"key":"ref_85","unstructured":"Fieser, M. (1971). Reagents for Organic Synthesis, John Wiley & Sons."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"12449","DOI":"10.1021\/jp802462x","article-title":"Synthesis, molecular structure, and EPR analysis of the three-coordinate Ni (I) complex [Ni (PPh3) 3][BF4]","volume":"112","author":"Saraev","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/0022-1759(86)90215-2","article-title":"Use of MTT colorimetric assay to measure cell activation","volume":"94","author":"Gerlier","year":"1986","journal-title":"J. Immunol. Methods"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/S1387-2656(05)11004-7","article-title":"Tetrazolium dyes as tools in cell biology: New insights into their cellular reduction","volume":"11","author":"Berridge","year":"2005","journal-title":"Biotechnol. Annu. Rev."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"1827","DOI":"10.1055\/s-0034-1380415","article-title":"Bis (indolyl) methane alkaloids: Isolation, bioactivity, and syntheses","volume":"47","author":"Praveen","year":"2015","journal-title":"Synthesis"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"2863","DOI":"10.1016\/j.bmcl.2007.02.059","article-title":"Novel bis (indolyl) maleimide pyridinophanes that are potent, selective inhibitors of glycogen synthase kinase-3","volume":"17","author":"Zhang","year":"2007","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1038\/9035","article-title":"Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases","volume":"1","author":"Hoessel","year":"1999","journal-title":"Nat. Cell Biol."},{"key":"ref_92","doi-asserted-by":"crossref","unstructured":"Schr\u00f6dinger, L. (2017). Schr\u00f6dinger Suite, Schr\u00f6dinger, LLC.","DOI":"10.2307\/j.ctvcm4h07.63"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/8\/2202\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T14:28:01Z","timestamp":1760365681000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/8\/2202"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,4,11]]},"references-count":92,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2021,4]]}},"alternative-id":["molecules26082202"],"URL":"https:\/\/doi.org\/10.3390\/molecules26082202","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2021,4,11]]}}}