{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T18:06:17Z","timestamp":1790618777776,"version":"4.1.0"},"reference-count":77,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2020,1,17]],"date-time":"2020-01-17T00:00:00Z","timestamp":1579219200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt\u2019s lymphoma (BL) is a rare form of non-Hodgkin\u2019s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG-75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2-nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV\u2212 MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17\u20130.38 \u03bcM against the BL cell line EBV\u2212 MUTU-1 and IC50 values in the range 0.45\u20130.78 \u03bcM against the chemoresistant BL cell line EBV+ DG-75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.<\/jats:p>","DOI":"10.3390\/ph13010016","type":"journal-article","created":{"date-parts":[[2020,1,20]],"date-time":"2020-01-20T04:27:09Z","timestamp":1579494429000},"page":"16","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Design, Synthesis and Biochemical Evaluation of Novel Ethanoanthracenes and Related Compounds to Target Burkitt\u2019s Lymphoma"],"prefix":"10.3390","volume":"13","author":[{"given":"Andrew J.","family":"Byrne","sequence":"first","affiliation":[{"name":"School of Pharmacy and Pharmaceutical Sciences, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandra A.","family":"Bright","sequence":"additional","affiliation":[{"name":"School of Biochemistry and Immunology, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"James P.","family":"McKeown","sequence":"additional","affiliation":[{"name":"School of Pharmacy and Pharmaceutical Sciences, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John E.","family":"O\u2019Brien","sequence":"additional","affiliation":[{"name":"School of Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brendan","family":"Twamley","sequence":"additional","affiliation":[{"name":"School of Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Darren","family":"Fayne","sequence":"additional","affiliation":[{"name":"School of Biochemistry and Immunology, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"D. Clive","family":"Williams","sequence":"additional","affiliation":[{"name":"School of Biochemistry and Immunology, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mary J.","family":"Meegan","sequence":"additional","affiliation":[{"name":"School of Pharmacy and Pharmaceutical Sciences, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, Dublin 2, D02 R590, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,1,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3009","DOI":"10.1182\/blood-2004-02-0405","article-title":"Adult Burkitt leukemia and lymphoma","volume":"104","author":"Blum","year":"2004","journal-title":"Blood"},{"key":"ref_2","first-page":"11","article-title":"Burkitt lymphoma in adolescents and young adults: Management challenges","volume":"8","author":"Dozzo","year":"2017","journal-title":"Adolesc. Health Med. Ther."},{"key":"ref_3","unstructured":"National Cancer Registry Ireland (2018). Cancer in Ireland 1994\u20132016 with Estimates for 2016\u20132018: Annual Report of the National Cancer Registry, NCRI."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1038\/sj.onc.1210668","article-title":"Two Epstein-Barr virus (EBV) oncoproteins cooperate to repress expression of the proapoptotic tumour-suppressor bim: Clues to the pathogenesis of Burkitt\u2019s lymphoma","volume":"27","author":"Anderton","year":"2008","journal-title":"Oncogene"},{"key":"ref_5","unstructured":"(2019, October 24). Phase II Study of Dose-Adjusted EPOCH-Rituximab in Adults with Untreated Burkitt Lymphoma and C-Myc+ Diffuse Large B-Cell Lymphoma-Full Text View-Clinicaltrials. Gov, Available online: Http:\/\/clinicaltrials.Gov\/ct2\/show\/nct01092182?Term=burkitt+lymphoma&rank=1."},{"key":"ref_6","unstructured":"(2019, October 24). Chemotherapy Plus Rituximab Combination for Adult Lymphoblastic Leukemia (B-ALL) and Burkitt\u2019s Non-Hodgkin Lymphoma-Full Text View-Clinicaltrials. Gov, Available online: Http:\/\/clinicaltrials.Gov\/ct2\/show\/nct01290120?Term=burkitt+lymphoma&rank=2."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1569","DOI":"10.1002\/cncr.21776","article-title":"Chemoimmunotherapy with hyper-cvad plus rituximab for the treatment of adult Burkitt and Burkitt-type lymphoma or acute lymphoblastic leukemia","volume":"106","author":"Thomas","year":"2006","journal-title":"Cancer"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1136\/jcp.2007.051953","article-title":"HIV infection and lymphoma","volume":"60","author":"Grogg","year":"2007","journal-title":"J. Clin. Pathol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"5600","DOI":"10.1182\/blood-2010-03-275917","article-title":"Aids-related Burkitt lymphoma in the United States: What do age and CD4 lymphocyte patterns tell us about etiology and\/or biology?","volume":"116","author":"Simard","year":"2010","journal-title":"Blood"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1002\/ijc.1427","article-title":"2-benzoxazolyl and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine: A novel class of antitumor agents","volume":"94","author":"Easmon","year":"2001","journal-title":"Int. J. Cancer"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1557","DOI":"10.1016\/j.biopha.2018.07.124","article-title":"Beta-elemene against Burkitt\u2019s lymphoma via activation of PUMA mediated apoptotic pathway","volume":"106","author":"Hu","year":"2018","journal-title":"Biomed. Pharmacother."},{"key":"ref_12","unstructured":"(2019, October 24). Lenalidomide and Blinatumomab in Treating Patients with Relapsed Non-Hodgkin Lymphoma, Available online: https:\/\/clinicaltrials.gov\/ct2\/show\/NCT02568553."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3317","DOI":"10.1038\/s41598-018-21570-z","article-title":"Shikonin exerts antitumor activity in Burkitt\u2019s lymphoma by inhibiting C-MYC and PI3K\/AKT\/mTOR pathway and acts synergistically with doxorubicin","volume":"8","author":"Ni","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1007\/s00280-003-0738-1","article-title":"Phenothiazines suppress proliferation and induce apoptosis in cultured leukemic cells without any influence on the viability of normal lymphocytes. Phenothiazines and leukemia","volume":"53","author":"Zhelev","year":"2004","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.taap.2012.05.014","article-title":"Necrox-7 prevents oxidative stress-induced cardiomyopathy by inhibition of nadph oxidase activity in rats","volume":"263","author":"Park","year":"2012","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2720","DOI":"10.1158\/1538-7445.AM2014-2720","article-title":"In vitro evaluation of a novel chemotherapeutic agent, NecroX-7, in human Burkitt lymphoma cells","volume":"74","author":"Kim","year":"2014","journal-title":"Cancer Res."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Gobec, M., Obreza, A., Prijatelj, M., Brus, B., Gobec, S., and Mlinaric-Rascan, I. (2012). Selective cytotoxicity of amidinopiperidine based compounds towards Burkitt\u2019s lymphoma cells involves proteasome inhibition. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0041961"},{"key":"ref_18","first-page":"75","article-title":"MYC as therapeutic target in leukemia and lymphoma","volume":"5","author":"Cortiguera","year":"2015","journal-title":"Blood Lymphat. Cancer Targets Ther."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Poole, C.J., Zheng, W., Lee, H., Young, D., Lodh, A., Chadli, A., and van Riggelen, J. (2018). Targeting the MYC oncogene in Burkitt lymphoma through HSP90 inhibition. Cancers, 10.","DOI":"10.3390\/cancers10110448"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"523","DOI":"10.3109\/10428190903552112","article-title":"The antidepressants maprotiline and fluoxetine have potent selective antiproliferative effects against Burkitt lymphoma independently of the norepinephrine and serotonin transporters","volume":"51","author":"Cloonan","year":"2010","journal-title":"Leuk. Lymphoma"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1712","DOI":"10.1002\/ijc.25477","article-title":"The antidepressants maprotiline and fluoxetine induce type II autophagic cell death in drug-resistant Burkitt\u2019s lymphoma","volume":"128","author":"Cloonan","year":"2011","journal-title":"Int. J. Cancer"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1096\/fj.04-3477fje","article-title":"The serotonin transporter (SLC6A4) is present in B-cell clones of diverse malignant origin: Probing a potential anti-tumor target for psychotropics","volume":"19","author":"Meredith","year":"2005","journal-title":"FASEB J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1002\/(SICI)1099-0461(1999)13:6<338::AID-JBT8>3.0.CO;2-7","article-title":"The antidepressants imipramine, clomipramine, and citalopram induce apoptosis in human acute myeloid leukemia HL-60 cells via caspase-3 activation","volume":"13","author":"Xia","year":"1999","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1002\/(SICI)1099-0461(1998)12:2<115::AID-JBT6>3.0.CO;2-O","article-title":"Modulation of apoptosis induced by tricyclic antidepressants in human peripheral lymphocytes","volume":"12","author":"Xia","year":"1998","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1016\/S0192-0561(97)00020-9","article-title":"Tricyclic antidepressants induce apoptosis in human T lymphocytes","volume":"19","author":"Xia","year":"1997","journal-title":"Int. J. Immunopharmacol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1039\/c0md00108b","article-title":"Redesigning the designer drug ecstasy: Non-psychoactive mdma analogues exhibiting Burkitt\u2019s lymphoma cytotoxicity","volume":"1","author":"Gandy","year":"2010","journal-title":"MedChemComm"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1016\/j.ejmech.2013.10.076","article-title":"Synthesis and antiproliferative action of a novel series of maprotiline analogues","volume":"71","author":"McNamara","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1259","DOI":"10.1021\/jm801589x","article-title":"Anthracene based compounds as new L-type Ca2+ channel blockers: Design, synthesis, and full biological profile","volume":"52","author":"Bova","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2139","DOI":"10.1016\/j.bmcl.2009.03.006","article-title":"Discovery of novel dihydro-9,10-ethano-anthracene carboxamides as glucocorticoid receptor modulators","volume":"19","author":"Yang","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"596","DOI":"10.1021\/acsmedchemlett.8b00594","article-title":"Polycyclic maleimide-based scaffold as new privileged structure for navigating the cannabinoid system opportunities","volume":"10","author":"Bisi","year":"2019","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1016\/j.ejmech.2015.01.004","article-title":"Design, synthesis and biological profile of new inhibitors of multidrug resistance associated proteins carrying a polycyclic scaffold","volume":"92","author":"Bisi","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/S0223-5234(03)00018-7","article-title":"Effects of a series of dihydroanthracene derivatives on drug efflux in multidrug resistant cancer cells","volume":"38","author":"Alibert","year":"2003","journal-title":"Eur. J. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1524","DOI":"10.1021\/acsinfecdis.9b00072","article-title":"Targeting the bacterial membrane with a new polycyclic privileged structure: A powerful tool to face staphylococcus aureus infections","volume":"5","author":"Bonvicini","year":"2019","journal-title":"ACS Infect. Dis."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3195","DOI":"10.1021\/jm011046l","article-title":"Synthesis and effects on chloroquine susceptibility in plasmodium falciparum of a series of new dihydroanthracene derivatives","volume":"45","author":"Alibert","year":"2002","journal-title":"J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"4278","DOI":"10.1007\/s00044-012-0439-6","article-title":"Synthesis, anti-inflammatory, and cytotoxicity evaluation of 9,10-dihydroanthracene-9,10-\u03b1, \u03b2-succinimide and bis-succinimide derivatives","volume":"22","author":"Arya","year":"2013","journal-title":"Med. Chem. Res."},{"key":"ref_36","unstructured":"Rossiter, S., Kirton, S.B., and Camara, R. (2016). Preparation of Substituted 3,4-(9\u2032, 10\u2032-dihydroanthracene-9\u2032,10\u2032-diyl) Succinimides as Inhibitors of S100P\/RAGE Interaction for Treating Pancreatic Cancer. (WO 2016181120 A1), PCT Int. Appl. (2016)."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6606","DOI":"10.1016\/j.bmc.2009.07.076","article-title":"E-combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory beta-E-nitrostyrenes","volume":"17","author":"Pettit","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"8073","DOI":"10.1016\/j.bmc.2006.07.035","article-title":"Synthesis and evaluation of alpha-hydroxymethylated conjugated nitroalkenes for their anticancer activity: Inhibition of cell proliferation by targeting microtubules","volume":"14","author":"Mohan","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1016\/S0006-2952(02)01618-0","article-title":"Structure activity analysis of the pro-apoptotic, antitumor effect of nitrostyrene adducts and related compounds","volume":"65","author":"Kaap","year":"2003","journal-title":"Biochem. Pharmacol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.ejphar.2011.12.031","article-title":"Autophagy inhibited Ehrlich ascitic tumor cells apoptosis induced by the nitrostyrene derivative compounds: Relationship with cytosolic calcium mobilization","volume":"678","author":"Calgarotto","year":"2012","journal-title":"Eur. J. Pharmacol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1007\/s002800050989","article-title":"The effect of antimicrotubule agents on signal transduction pathways of apoptosis: A review","volume":"44","author":"Wang","year":"1999","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"6751","DOI":"10.1021\/jm200639r","article-title":"Design and synthesis of resveratrol-based nitrovinylstilbenes as antimitotic agents","volume":"54","author":"Reddy","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"18106","DOI":"10.18632\/oncotarget.14996","article-title":"3\u2032-Hydroxy-4\u2032-methoxy-beta-methyl-beta-nitrostyrene inhibits tumorigenesis in colorectal cancer cells through ROS-mediated DNA damage and mitochondrial dysfunction","volume":"8","author":"Tsai","year":"2017","journal-title":"Oncotarget"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1016\/j.canlet.2015.11.035","article-title":"The synthetic beta-nitrostyrene derivative CYT-Rx20 induces breast cancer cell death and autophagy via ROS-mediated MEK\/ERK pathway","volume":"371","author":"Hung","year":"2016","journal-title":"Cancer Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"7621","DOI":"10.1016\/j.bmc.2010.08.039","article-title":"The synthesis and biologic evaluation of anti-platelet and cytotoxic beta-nitrostyrenes","volume":"18","author":"Hsieh","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1142","DOI":"10.1074\/jbc.M113.515080","article-title":"3,4-methylenedioxy-beta-nitrostyrene inhibits NLRP3 inflammasome activation by blocking assembly of the inflammasome","volume":"289","author":"He","year":"2014","journal-title":"J. Biol. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1081\/IPH-120003749","article-title":"The effect of nitrostyrene on cell proliferation and macrophage immune responses","volume":"24","author":"Carter","year":"2002","journal-title":"Immunopharmacol. Immunotoxicol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2049","DOI":"10.1158\/0008-5472.CAN-14-2435","article-title":"Nitrostyrene derivatives act as RXRalpha ligands to inhibit TNFalpha Activation of NF-kappaB","volume":"75","author":"Zeng","year":"2015","journal-title":"Cancer Res."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1016\/j.bmc.2010.11.054","article-title":"Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents","volume":"19","author":"McNamara","year":"2011","journal-title":"Bioorg. Med. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"181","DOI":"10.2174\/1573406413666171002123907","article-title":"Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in burkitt\u2019s lymphoma","volume":"14","author":"Byrne","year":"2018","journal-title":"Med. Chem."},{"key":"ref_51","first-page":"3127","article-title":"Selected nitrostyrene compounds demonstrate potent activity in chronic lymphocytic leukaemia cells, including those with poor prognostic markers","volume":"41","author":"Bright","year":"2019","journal-title":"Oncol. Rep."},{"key":"ref_52","unstructured":"(2019, October 24). Research Council of Lithuania, Crystallography Open Database. Available online: http:\/\/www.crystallography.net\/cod\/2003498.html."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"7281","DOI":"10.1021\/jo00026a018","article-title":"Modular design of hosts involving a rigid succinimide framework and N-bonded lateral groups. Crystalline inclusion properties and crystal structures of inclusion compounds with dioxane, MeOH, and DMF","volume":"56","author":"Weber","year":"1991","journal-title":"J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"4939","DOI":"10.1021\/jo00394a040","article-title":"Regioselectivity in the Diels-Alder reaction of 9-substituted anthracenes","volume":"44","author":"Alston","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1693","DOI":"10.1021\/ja00760a044","article-title":"Application of electron spin resonance spectroscopy to problems of structure and conformation. XXIV. Aliphatic semidiones. XIX. Polycyclic derivatives of cyclobutanesemidione","volume":"94","author":"Russell","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1585","DOI":"10.1246\/bcsj.79.1585","article-title":"Deamination of 1-alkyl-9-aminomethyltriptycenes. Participation of a neighboring 1-alkyl substituent","volume":"79","author":"Yamamoto","year":"2006","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"12","DOI":"10.15227\/orgsyn.048.0012","article-title":"Benzenediazonium-2-carboxylate and biphenylene","volume":"48","author":"Logullo","year":"1968","journal-title":"Org. Synth."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1549","DOI":"10.1021\/ja00893a045","article-title":"Benzynes via aprotic diazotization of anthranilic acids: A convenient synthesis of triptycene and derivatives","volume":"85","author":"Friedman","year":"1963","journal-title":"J. Am. Chem. Soc."},{"key":"ref_59","first-page":"663","article-title":"Chemistry of dibenzobarallene","volume":"35","author":"Gouda","year":"2011","journal-title":"Turk. J. Chem."},{"key":"ref_60","first-page":"1323","article-title":"Deamination of certain amines with amino group at the substituent in the head of a triptycene molecule bridge","volume":"225","author":"Brunovlenskaya","year":"1975","journal-title":"Dokl. Akad. Nauk. SSSR"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1385","DOI":"10.1002\/hlca.19690520602","article-title":"Synthesis and properties of 1-aminoalkyl-dibenzo(b,e)bicyclo(2,2,2) octadienes","volume":"52","author":"Wilhelm","year":"1969","journal-title":"Helv. Chim. Acta"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"3223","DOI":"10.1021\/jo00366a035","article-title":"Photochemical isomerization and dimerization of 1-(9-anthryl)-2-nitroethylene","volume":"51","author":"Becker","year":"1986","journal-title":"J. Org. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1246\/cl.2000.454","article-title":"Deamination of 1-alkyl-9-aminomethyltriptycenes: Participation of the \u03b1-C-H bond of the 1-alkyl group","volume":"29","author":"Yamamoto","year":"2000","journal-title":"Chem. Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2956","DOI":"10.1021\/jo00365a019","article-title":"Synthesis and photochemical isomerization of 1,2-di-9-anthrylethanol and 1,2-di-9-anthrylethanone","volume":"51","author":"Becker","year":"1986","journal-title":"J. Org. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"6693","DOI":"10.1016\/j.tet.2005.05.017","article-title":"Synthesis and reactions of a monosubstituted dithiirane 1-oxide, 3-(9-triptycyl) dithiirane 1-oxide","volume":"61","author":"Ishii","year":"2005","journal-title":"Tetrahedron"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1066","DOI":"10.1139\/v99-092","article-title":"Spectroscopic studies on effects of triptycyl group on structures and reactivities of triplet arylcarbenes","volume":"77","author":"Tomioka","year":"1999","journal-title":"Can. J. Chem."},{"key":"ref_67","unstructured":"Sauers, C.K., and Cotter, R.J. (1962). Preparation of Maleimides. (3018290 A), U.S. Patent."},{"key":"ref_68","first-page":"216","article-title":"Relation between chemical structure and antimicrobial and insecticidal activities in organonitro compounds. VIII. Synthesis of heterocyclic nitroalkene derivatives and their activities","volume":"13","author":"Koremura","year":"1961","journal-title":"Takamine Kenkyusho Nenpo"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1071\/CH9890593","article-title":"Photochemical cis-trans isomerization of 2-substituted 9-(2-nitroethenyl)anthracenes. X-ray structure analyses of (E)-and (Z)-9-(2-nitro-2-phenylethenyl)anthracene","volume":"42","author":"Becker","year":"1989","journal-title":"Aust. J. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"8457","DOI":"10.1016\/0040-4039(95)01821-X","article-title":"Synthesis of a tetrakis(9-anthryl) substituted porphyrin and intramolecular charge-transfer emission in its dication","volume":"36","author":"Nakajima","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_71","unstructured":"(2015). Molecular Operating Environment (MOE), 2015.10, Chemical Computing Group Inc.. Available online: https:\/\/www.chemcomp.com\/Products.html."},{"key":"ref_72","unstructured":"(2012). Bruker APEX2 v2012.12-0, Bruker AXS Inc.. Available online: https:\/\/www.bruker.com\/nc\/search.html?q=Bruker%20APEX2%202012.12-0;&resetPager=1."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. A"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELX","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. C Struct. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"ref_76","unstructured":"(2020, January 16). SADABS, Area Detector Absorption Correction Program, Sheldrick, G.M. University of G\u00f6ttingen, Germany, 2014. Available online: https:\/\/journals.iucr.org\/e\/services\/stdswrefs.html."},{"key":"ref_77","first-page":"148","article-title":"Structure validation in chemical crystallography","volume":"D65","author":"Spek","year":"2009","journal-title":"Acta Cryst."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/13\/1\/16\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T13:43:52Z","timestamp":1760363032000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/13\/1\/16"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,1,17]]},"references-count":77,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2020,1]]}},"alternative-id":["ph13010016"],"URL":"https:\/\/doi.org\/10.3390\/ph13010016","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,1,17]]}}}