{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T18:43:30Z","timestamp":1790880210366,"version":"4.1.0"},"reference-count":92,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2023,4,1]],"date-time":"2023-04-01T00:00:00Z","timestamp":1680307200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2023,4,1]],"date-time":"2023-04-01T00:00:00Z","timestamp":1680307200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2023,3,23]],"date-time":"2023-03-23T00:00:00Z","timestamp":1679529600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100008667","name":"National Cancer Research Institute","doi-asserted-by":"publisher","award":["LX22NPO5102"],"award-info":[{"award-number":["LX22NPO5102"]}],"id":[{"id":"10.13039\/100008667","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100014434","name":"NAWA","doi-asserted-by":"publisher","award":["BPI\/PST\/2021\/1\/00002\/U\/00001"],"award-info":[{"award-number":["BPI\/PST\/2021\/1\/00002\/U\/00001"]}],"id":[{"id":"10.13039\/501100014434","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100018227","name":"National Research Foundation of Ukraine","doi-asserted-by":"publisher","award":["CZ-OPENSCREEN \\u2013 LM2023052"],"award-info":[{"award-number":["CZ-OPENSCREEN \\u2013 LM2023052"]}],"id":[{"id":"10.13039\/100018227","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008690","name":"National Research Foundation of Ukraine","doi-asserted-by":"publisher","award":["2020.02\/0035"],"award-info":[{"award-number":["2020.02\/0035"]}],"id":[{"id":"10.13039\/501100008690","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2023,4]]},"DOI":"10.1016\/j.ejmech.2023.115304","type":"journal-article","created":{"date-parts":[[2023,3,23]],"date-time":"2023-03-23T21:47:44Z","timestamp":1679608064000},"page":"115304","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":34,"special_numbering":"C","title":["Molecular design, synthesis and anticancer activity of new thiopyrano[2,3-d]thiazoles based on 5-hydroxy-1,4-naphthoquinone (juglone)"],"prefix":"10.1016","volume":"252","author":[{"given":"Iryna","family":"Ivasechko","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrii","family":"Lozynskyi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julia","family":"Senkiv","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Piotr","family":"Roszczenko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuliia","family":"Kozak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nataliya","family":"Finiuk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga","family":"Klyuchivska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nataliya","family":"Kashchak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nazar","family":"Manko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zvenyslava","family":"Maslyak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Danylo","family":"Lesyk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andriy","family":"Karkhut","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Svyatoslav","family":"Polovkovych","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Czarnomysy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga","family":"Szewczyk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andriy","family":"Kozytskiy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olexandr","family":"Karpenko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dmytro","family":"Khyluk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrzej","family":"Gzella","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Krzysztof","family":"Bielawski","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Bielawska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Petr","family":"Dzubak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sona","family":"Gurska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marian","family":"Hajduch","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rostyslav","family":"Stoika","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3322-0080","authenticated-orcid":false,"given":"Roman","family":"Lesyk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2023.115304_bib1","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1016\/j.chroma.2016.06.009","article-title":"A strategy for screening active lead compounds and functional compound combinations from herbal medicines based on pharmacophore filtering and knockout\/knockin chromatography","volume":"1456","author":"Song","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.ejmech.2023.115304_bib2","doi-asserted-by":"crossref","first-page":"27355","DOI":"10.1039\/D2RA03624J","article-title":"Novel thiazole derivatives incorporating phenyl sulphonyl moiety as potent BRAFV600E kinase inhibitors targeting melanoma","volume":"12","author":"Khormi","year":"2022","journal-title":"RSC Adv."},{"key":"10.1016\/j.ejmech.2023.115304_bib3","first-page":"355","article-title":"Design, synthesis, cytotoxicity, and molecular docking studies of novel thiazolyl\u2013hydrazone derivatives as histone lysine acetyl-transferase inhibitors and apoptosis inducers","author":"Abbas","year":"2022","journal-title":"Arch. Pharm."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib4","doi-asserted-by":"crossref","first-page":"1878","DOI":"10.1016\/j.arabjc.2022.103782","article-title":"Fluorinated azole anticancer drugs: synthesis, elaborated structure elucidation and docking studies","volume":"15","author":"Alsaedi","year":"2022","journal-title":"Arab. J. Chem."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib5","doi-asserted-by":"crossref","first-page":"26","DOI":"10.3390\/scipharm86020026","article-title":"Thiopyrano[2,3-d]thiazoles as new efficient scaffolds in medicinal chemistry","volume":"86","author":"Kryshchyshyn","year":"2018","journal-title":"Sci. Pharm."},{"issue":"15","key":"10.1016\/j.ejmech.2023.115304_bib6","doi-asserted-by":"crossref","first-page":"5230","DOI":"10.1016\/j.bmc.2006.03.053","article-title":"Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies","volume":"14","author":"Lesyk","year":"2006","journal-title":"Bioorg. Med. Chem."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib7","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1080\/00397911.2013.800552","article-title":"5-Ethoxymethylidene-4-thioxo-2-thiazolidinone as versatile building block for novel biorelevant small molecules with thiopyrano[2,3-d][1,3]thiazole core","volume":"44","author":"Atamanyuk","year":"2014","journal-title":"Synth. Commun."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib8","first-page":"131","article-title":"Screening of antioxidant and anti-inflammatory activities among thiopyrano[2,3-d]thiazoles, Biopolym","volume":"31","author":"Lozynskyi","year":"2015","journal-title":"Cell"},{"issue":"9","key":"10.1016\/j.ejmech.2023.115304_bib9","first-page":"1245","article-title":"Synthesis, anticancer and antiviral activities of novel thiopyrano[2,3-d]thiazole-6-carbaldehydes, Phosphorus Sulfur Silicon Relat","volume":"191","author":"Lozynskyi","year":"2016","journal-title":"Elements"},{"issue":"23","key":"10.1016\/j.ejmech.2023.115304_bib10","doi-asserted-by":"crossref","first-page":"7071","DOI":"10.1016\/j.bmcl.2012.09.091","article-title":"Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles, Bioorg","volume":"22","author":"Zelisko","year":"2012","journal-title":"Med. Chem. Lett."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib11","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1080\/17415993.2014.933341","article-title":"A simple green synthesis of (Z)-5-arylmethylene-4-thioxothiazolidines and thiopyrano[2,3-d]thiazolidine-2-thiones in PEG-400 under catalyst-free conditions","volume":"35","author":"Metwally","year":"2014","journal-title":"J. Sulphur Chem."},{"key":"10.1016\/j.ejmech.2023.115304_bib12","doi-asserted-by":"crossref","first-page":"432","DOI":"10.1055\/s-1985-31232","article-title":"Substituted acrylonitriles in heterocyclic synthesis. The reaction of \u03b1-substituted \u03b2-(2-furyl)-acrylonitriles with some active-methylene heterocycles","volume":"4","author":"Abdelrazek","year":"1985","journal-title":"Synthesis"},{"key":"10.1016\/j.ejmech.2023.115304_bib13","doi-asserted-by":"crossref","DOI":"10.1016\/j.molstruc.2022.132574","article-title":"Synthesis and structure elucidation of thiopyrano[2,3-d]thiazole-6-carbonitriles as adducts of Michael reaction\u0431","volume":"1256","author":"Lozynskyi","year":"2022","journal-title":"J. Mol. Struct."},{"key":"10.1016\/j.ejmech.2023.115304_bib14","doi-asserted-by":"crossref","DOI":"10.1016\/j.molstruc.2020.128448","article-title":"Synthesis of new structurally diverse thiazolidinone-derived compounds based on reaction of isorhodanine with ortho-substituted aldehydes, \u03b1-keto-and \u03b2-aroylacrylic acids","volume":"1217","author":"Lozynskyi","year":"2020","journal-title":"J. Mol. Struct."},{"issue":"6","key":"10.1016\/j.ejmech.2023.115304_bib15","doi-asserted-by":"crossref","first-page":"1294","DOI":"10.3390\/nu11061294","article-title":"Comparison of the effect of native 1, 4-naphthoquinones plumbagin, menadione, and lawsone on viability, redox status, and mitochondrial functions of C6 glioblastoma cells","volume":"11","author":"Majiene","year":"2019","journal-title":"Nutrients"},{"issue":"12","key":"10.1016\/j.ejmech.2023.115304_bib16","doi-asserted-by":"crossref","first-page":"1029","DOI":"10.1248\/cpb.c15-00607","article-title":"Design, synthesis, biological evaluation, and antioxidant and cytotoxic activity of heteroatom-substituted 1, 4-naphtho-and benzoquinones","volume":"63","author":"Deniz","year":"2015","journal-title":"Chem. Pharm. Bull."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib17","doi-asserted-by":"crossref","first-page":"107","DOI":"10.3109\/14756366.2014.892935","article-title":"2-Chloro-1,4-naphthoquinone derivative of quercetin as an inhibitor of aldose reductase and anti-inflammatory agent","volume":"30","author":"Milackova","year":"2015","journal-title":"J. Enzym. Inhib. Med. Chem."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib18","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s12935-019-0925-8","article-title":"The diverse mechanisms and anticancer potential of naphthoquinones","volume":"19","author":"Pereyra","year":"2019","journal-title":"Cancer Cell Int."},{"issue":"9","key":"10.1016\/j.ejmech.2023.115304_bib19","doi-asserted-by":"crossref","first-page":"1087","DOI":"10.1517\/13543776.2013.798303","article-title":"Recent development on naphthoquinone derivatives and their therapeutic applications as anticancer agents","volume":"23","author":"Tandon","year":"2013","journal-title":"Expert Opin. Ther. Pat."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib20","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1021\/np2006499","article-title":"Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma cells","volume":"75","author":"Kretschmer","year":"2012","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.ejmech.2023.115304_bib21","doi-asserted-by":"crossref","first-page":"1813","DOI":"10.1007\/s11164-016-2732-3","article-title":"Synthesis and studies of the antifungal activity of 2-anilino-\/2,3-dianilino-\/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones","volume":"43","author":"Leyva","year":"2017","journal-title":"Res. Chem. Intermed."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib22","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1007\/s12272-012-0103-1","article-title":"Antitrypanosomal activities and cytotoxicity of some novel imidosubstituted 1,4-naphthoquinone derivatives","volume":"35","author":"Khraiwesh","year":"2012","journal-title":"Arch Pharm. Res. (Seoul)"},{"issue":"22","key":"10.1016\/j.ejmech.2023.115304_bib23","doi-asserted-by":"crossref","first-page":"2018","DOI":"10.2174\/1568026621666210804121054","article-title":"Juglone: a versatile natural platform for obtaining new bioactive compounds","volume":"21","author":"dos S Moreira","year":"2021","journal-title":"Curr. Top. Med. Chem."},{"key":"10.1016\/j.ejmech.2023.115304_bib24","doi-asserted-by":"crossref","DOI":"10.1016\/j.biopha.2022.112785","article-title":"Molecular biological mechanism of action in cancer therapies: juglone and its derivatives, the future of development","volume":"148","author":"Tang","year":"2022","journal-title":"Biomed. Pharmacother."},{"issue":"4","key":"10.1016\/j.ejmech.2023.115304_bib25","doi-asserted-by":"crossref","first-page":"91","DOI":"10.3390\/antiox8040091","article-title":"Juglone in oxidative stress and cell signaling","volume":"8","author":"Ahmad","year":"2019","journal-title":"Antioxidants"},{"issue":"3","key":"10.1016\/j.ejmech.2023.115304_bib26","first-page":"1","article-title":"A summary of extraction, synthesis, properties, and potential uses of juglone: a literature review","volume":"13","author":"Strugstad","year":"2012","journal-title":"J. Ecosyst. Manag."},{"issue":"8","key":"10.1016\/j.ejmech.2023.115304_bib27","doi-asserted-by":"crossref","first-page":"784","DOI":"10.3390\/agriculture11080784","article-title":"Is juglone the only naphthoquinone in Juglans regia L. with allelopathic effects?","volume":"11","author":"Medic","year":"2021","journal-title":"Agriculture"},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib28","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.taap.2005.03.005","article-title":"The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts","volume":"209","author":"Paulsen","year":"2005","journal-title":"Toxicol. Appl. Pharmacol."},{"issue":"10","key":"10.1016\/j.ejmech.2023.115304_bib29","first-page":"11162","article-title":"Pathologic role of peptidyl-prolyl isomerase Pin1 in pulmonary artery remodeling","volume":"13","author":"Wu","year":"2021","journal-title":"Am. J. Transl. Res."},{"issue":"11","key":"10.1016\/j.ejmech.2023.115304_bib30","doi-asserted-by":"crossref","first-page":"4947","DOI":"10.1039\/D1FO00790D","article-title":"Juglone, a novel activator of ferroptosis, induces cell death in endometrial carcinoma Ishikawa cells","volume":"12","author":"Zhang","year":"2021","journal-title":"Food Funct."},{"issue":"26","key":"10.1016\/j.ejmech.2023.115304_bib31","doi-asserted-by":"crossref","first-page":"7378","DOI":"10.1021\/acs.jafc.9b02759","article-title":"Mechanism of juglone-induced cell cycle arrest and apoptosis in Ishikawa human endometrial cancer cells","volume":"67","author":"Zhang","year":"2019","journal-title":"J. Agric. Food Chem."},{"issue":"6","key":"10.1016\/j.ejmech.2023.115304_bib32","doi-asserted-by":"crossref","first-page":"460","DOI":"10.1111\/bcpt.12340","article-title":"Enhanced eryptosis following juglone exposure","volume":"116","author":"Calabr\u00f2","year":"2015","journal-title":"Basic Clin. Pharmacol. Toxicol."},{"issue":"11","key":"10.1016\/j.ejmech.2023.115304_bib33","doi-asserted-by":"crossref","first-page":"1553","DOI":"10.1139\/y2012-134","article-title":"Anticancer activity and mechanism of juglone on human cervical carcinoma HeLa cells","volume":"90","author":"Zhang","year":"2012","journal-title":"Can. J. Physiol. Pharmacol."},{"issue":"21","key":"10.1016\/j.ejmech.2023.115304_bib34","doi-asserted-by":"crossref","first-page":"7575","DOI":"10.3390\/molecules27217575","article-title":"1,4-Naphthoquinone motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds","volume":"27","author":"Lozynskyi","year":"2022","journal-title":"Molecules"},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib35","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1515\/hc-2014-0204","article-title":"Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds","volume":"21","author":"Lozynskyi","year":"2015","journal-title":"Heterocycl. Commun."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib36","doi-asserted-by":"crossref","first-page":"906","DOI":"10.1002\/(SICI)1521-3765(20000303)6:5<906::AID-CHEM906>3.0.CO;2-G","article-title":"Enantioselective Diels\u2010Alder approach to C\u20103\u2010oxygenated angucyclinones from (SS)\u20102\u2010(p\u2010tolylsulfinyl)\u20101,4\u2010naphthoquinone","volume":"6","author":"Carre\u00f1o","year":"2000","journal-title":"Chem. Eur J."},{"issue":"41","key":"10.1016\/j.ejmech.2023.115304_bib37","doi-asserted-by":"crossref","first-page":"8592","DOI":"10.1039\/C5CC00623F","article-title":"Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones","volume":"51","author":"Magar","year":"2015","journal-title":"Chem. Commun. (J. Chem. Soc. Sect. D)"},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib38","doi-asserted-by":"crossref","first-page":"187","DOI":"10.17344\/acsi.2021.7123","article-title":"Synthesis of new regioisomers of 5-nitro-1,4-naphthoquinone, evaluation of antioxidant and catalase inhibition activities","volume":"69","author":"Abdassalam","year":"2022","journal-title":"Acta Chim. Slov."},{"key":"10.1016\/j.ejmech.2023.115304_bib39","first-page":"148","article-title":"Structure validation in chemical crystallography","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Crystallogr."},{"issue":"12","key":"10.1016\/j.ejmech.2023.115304_bib40","doi-asserted-by":"crossref","first-page":"S1","DOI":"10.1039\/p298700000s1","article-title":"Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds","volume":"2","author":"Allen","year":"1987","journal-title":"J. Chem. Soc. Perkin Trans."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib41","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1002\/ddr.430340203","article-title":"Some practical considerations and applications of the national cancer Institute in vitro anticancer drug discovery screen","volume":"34","author":"Boyd","year":"1995","journal-title":"Drug Dev. Res."},{"issue":"10","key":"10.1016\/j.ejmech.2023.115304_bib42","doi-asserted-by":"crossref","first-page":"813","DOI":"10.1038\/nrc1951","article-title":"The NCI60 human tumour cell line anticancer drug screen","volume":"6","author":"Shoemaker","year":"2006","journal-title":"Nat. Rev. Cancer"},{"key":"10.1016\/j.ejmech.2023.115304_bib43","series-title":"Anticancer Drug Development Guide. Cancer Drug Discov. Dev","first-page":"41","article-title":"The NCI in vitro anticancer drug discovery (60-cell) screen","author":"Boyd","year":"2004"},{"issue":"24","key":"10.1016\/j.ejmech.2023.115304_bib44","doi-asserted-by":"crossref","first-page":"1853","DOI":"10.1093\/jnci\/86.24.1853","article-title":"Use of the Kohonen self-organizing map to study the mechanisms of action of chemotherapeutic agents","volume":"86","author":"Van Osdol","year":"1994","journal-title":"J. Natl. Cancer Inst."},{"issue":"29","key":"10.1016\/j.ejmech.2023.115304_bib45","doi-asserted-by":"crossref","first-page":"46433","DOI":"10.18632\/oncotarget.10184","article-title":"A mechanism for 1,4-benzoquinone-induced genotoxicity","volume":"7","author":"Son","year":"2016","journal-title":"Oncotarget"},{"issue":"14","key":"10.1016\/j.ejmech.2023.115304_bib46","doi-asserted-by":"crossref","first-page":"7633","DOI":"10.1021\/acs.jmedchem.0c00512","article-title":"Bifunctional naphtho[2,3-d][1,2,3]triazole-4,9-dione compounds exhibit antitumor effects in vitro and in vivo by inhibiting dihydroorotate dehydrogenase and inducing reactive oxygen species production","volume":"63","author":"Zuo","year":"2020","journal-title":"J. Med. Chem."},{"issue":"18","key":"10.1016\/j.ejmech.2023.115304_bib47","doi-asserted-by":"crossref","first-page":"4494","DOI":"10.1021\/jm0400247","article-title":"Identification of 1,5-naphthyridine derivatives as a novel series of potent and selective TGF-\u03b2 type I receptor inhibitors","volume":"47","author":"Gellibert","year":"2004","journal-title":"J. Med. Chem."},{"issue":"1\u20133","key":"10.1016\/j.ejmech.2023.115304_bib48","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.ejphar.2008.05.030","article-title":"Doxorubicin inhibits TGF-beta signaling in human lung carcinoma A549 cells","volume":"590","author":"Filyak","year":"2008","journal-title":"Eur. J. Pharmacol."},{"issue":"6","key":"10.1016\/j.ejmech.2023.115304_bib49","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1016\/j.copbio.2007.09.006","article-title":"DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action","volume":"18","author":"Palchaudhuri","year":"2007","journal-title":"Curr. Opin. Biotechnol."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib50","doi-asserted-by":"crossref","first-page":"127","DOI":"10.2174\/0929867053363414","article-title":"The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work","volume":"12","author":"Mart\u00ednez","year":"2005","journal-title":"Curr. Med. Chem."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib51","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.mrgentox.2009.06.005","article-title":"A novel and simple method of screening compounds for interaction with DNA: a validation study","volume":"678","author":"Garas","year":"2009","journal-title":"Mutat. Res., Genet. Toxicol. Environ. Mutagen."},{"key":"10.1016\/j.ejmech.2023.115304_bib52","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jphotobiol.2013.03.013","article-title":"Drug\u2013DNA interactions and their study by UV\u2013Visible, fluorescence spectroscopies and cyclic voltametry","volume":"124","author":"Sirajuddin","year":"2013","journal-title":"J. Photochem. Photobiol., A"},{"key":"10.1016\/j.ejmech.2023.115304_bib53","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1007\/978-981-13-1477-3_10","article-title":"Natural lovastatin (NL) as an anticancer agent: docking and experimental studies","author":"Saibaba","year":"2019","journal-title":"ICTMI 2017"},{"issue":"4","key":"10.1016\/j.ejmech.2023.115304_bib54","doi-asserted-by":"crossref","first-page":"348","DOI":"10.20892\/j.issn.2095-3941.2017.0033","article-title":"Cell cycle regulation and anticancer drug discovery","volume":"14","author":"Bai","year":"2017","journal-title":"Cancer Biol. Med."},{"key":"10.1016\/j.ejmech.2023.115304_bib55","first-page":"7","article-title":"DNA content measurement for DNA ploidy and cell cycle analysis","volume":"1","author":"Darzynkiewicz","year":"1997","journal-title":"Curr Protoc Cytom"},{"issue":"7","key":"10.1016\/j.ejmech.2023.115304_bib56","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1016\/S0092-8674(01)00611-0","article-title":"XBP1 mRNA is induced by ATF6 and spliced by IRE1 in response to ER stress to produce a highly active transcription factor","volume":"107","author":"Yoshida","year":"2001","journal-title":"Cell"},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib57","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/j.molcel.2017.06.017","article-title":"The unfolded protein response and cell fate control","volume":"69","author":"Hetz","year":"2018","journal-title":"Mol. Cell"},{"key":"10.1016\/j.ejmech.2023.115304_bib58","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1038\/s41580-018-0089-8","article-title":"Regulation of apoptosis in health and disease: the balancing act of BCL-2 family proteins","volume":"20","author":"Singh","year":"2019","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"10.1016\/j.ejmech.2023.115304_bib59","doi-asserted-by":"crossref","DOI":"10.3389\/fcell.2020.620081","article-title":"Mitochondrial ion channels of the inner membrane and their regulation in cell death signaling","volume":"8","author":"Urbani","year":"2021","journal-title":"Front. Cell Dev. Biol."},{"issue":"11","key":"10.1016\/j.ejmech.2023.115304_bib60","doi-asserted-by":"crossref","first-page":"5581","DOI":"10.3390\/ijms22115581","article-title":"Mechanism of anticancer action of novel imidazole platinum(II) complex conjugated with G2 PAMAM-OH dendrimer in breast cancer cells","volume":"22","author":"Czarnomysy","year":"2021","journal-title":"Int. J. Mol. Sci."},{"issue":"17","key":"10.1016\/j.ejmech.2023.115304_bib61","doi-asserted-by":"crossref","first-page":"4304","DOI":"10.3390\/cancers14174304","article-title":"Novel selenoesters as a potential tool in triple-negative breast cancer treatment","volume":"14","author":"Radomska","year":"2022","journal-title":"Cancers"},{"issue":"4","key":"10.1016\/j.ejmech.2023.115304_bib62","doi-asserted-by":"crossref","DOI":"10.20900\/immunometab20200030","article-title":"White adipose tissue and cancer: impacts of doxorubicin and potential Co-therapies","volume":"2","author":"Biondo","year":"2020","journal-title":"Immunometabolism"},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib63","doi-asserted-by":"crossref","DOI":"10.1111\/apha.13400","article-title":"Doxorubicin-induced skeletal muscle atrophy: elucidating the underlying molecular pathways","volume":"229","author":"Hiensch","year":"2020","journal-title":"Acta Physiol."},{"issue":"4","key":"10.1016\/j.ejmech.2023.115304_bib64","doi-asserted-by":"crossref","first-page":"2057","DOI":"10.3892\/mmr.2017.6272","article-title":"A herbal formula, SYKT, reverses doxorubicin-induced myelosuppression and cardiotoxicity by inhibiting ROS-mediated apoptosis","volume":"15","author":"Chen","year":"2017","journal-title":"Mol. Med. Rep."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib65","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/j.critrevonc.2009.03.004","article-title":"CIPOMO investigators, Incidence and clinical impact of chemotherapy induced myelotoxicity in cancer patients: an observational retrospective survey","volume":"72","author":"Repetto","year":"2009","journal-title":"Crit. Rev. Oncol. Hematol."},{"issue":"3","key":"10.1016\/j.ejmech.2023.115304_bib66","doi-asserted-by":"crossref","first-page":"716","DOI":"10.1007\/s12032-010-9512-5","article-title":"Chemotherapy use and risk of bone marrow suppression in a large population-based cohort of older women with breast and ovarian cancer","volume":"28","author":"Nurgalieva","year":"2011","journal-title":"Med. Oncol."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib67","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1053\/j.seminoncol.2005.11.003","article-title":"Myelotoxicity from chemotherapy","volume":"33","author":"Daniel","year":"2006","journal-title":"Semin. Oncol."},{"key":"10.1016\/j.ejmech.2023.115304_bib68","doi-asserted-by":"crossref","DOI":"10.1016\/j.taap.2020.115380","article-title":"Co-administration of Luteolin mitigated toxicity in rats' lungs associated with doxorubicin treatment","volume":"411","author":"Owumi","year":"2021","journal-title":"Toxicol. Appl. Pharmacol."},{"issue":"6","key":"10.1016\/j.ejmech.2023.115304_bib69","doi-asserted-by":"crossref","DOI":"10.1111\/jfbc.13747","article-title":"Immunomodulatory effects of bee pollen on doxorubicin-induced bone marrow\/spleen immunosuppression in rat","volume":"45","author":"Shaldoum","year":"2021","journal-title":"J. Food Biochem."},{"issue":"11","key":"10.1016\/j.ejmech.2023.115304_bib70","doi-asserted-by":"crossref","first-page":"5785","DOI":"10.7314\/APJCP.2012.13.11.5785","article-title":"Immunomodulatory effects of hexane insoluble fraction of Ficus septica Burm. F. in doxorubicin-treated rats","volume":"13","author":"Nugroho","year":"2012","journal-title":"Asian Pac. J. Cancer Prev. APJCP"},{"key":"10.1016\/j.ejmech.2023.115304_bib71","article-title":"Selective cytoprotective effect of histamine on doxorubicin-induced hepatic and cardiac toxicity in animal models","volume":"1","author":"Lamas","year":"2015","journal-title":"Cell Death Dis."},{"issue":"6","key":"10.1016\/j.ejmech.2023.115304_bib72","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.1016\/j.yjmcc.2012.03.006","article-title":"Doxorubicin-induced cardiomyopathy: from molecular mechanisms to therapeutic strategies","volume":"52","author":"Octavia","year":"2012","journal-title":"J. Mol. Cell. Cardiol."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib73","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1124\/pr.56.2.6","article-title":"Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity","volume":"56","author":"Minotti","year":"2004","journal-title":"Pharmacol. Rev."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib74","doi-asserted-by":"crossref","first-page":"3953","DOI":"10.3892\/mmr.2016.5017","article-title":"Protective effect of berberine on doxorubicin-induced acute hepatorenal toxicity in rats","volume":"13","author":"Chen","year":"2016","journal-title":"Mol. Med. Rep."},{"key":"10.1016\/j.ejmech.2023.115304_bib75","doi-asserted-by":"crossref","DOI":"10.1016\/j.lfs.2020.117599","article-title":"New molecular and biochemical insights of doxorubicin-induced hepatotoxicity","volume":"250","author":"Prasanna","year":"2020","journal-title":"Life Sci."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib76","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s40959-019-0037-6","article-title":"Systemic and cardiac susceptibility of immune compromised mice to doxorubicin","volume":"5","author":"Favreau-Lessard","year":"2019","journal-title":"Cardio-Oncology"},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib77","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1007\/BF00481594","article-title":"4-Thiazolidines, derivatives and analogs: V. arylidene derivatives of isorhodanine","volume":"3","author":"Komaritsa","year":"1967","journal-title":"Chem. Heterocycl. Compd."},{"key":"10.1016\/j.ejmech.2023.115304_bib78","first-page":"1385","article-title":"Isorhodanine and thiorhodanine motifs in the synthesis of fused thiopyrano[2,3-d][1,3]thiazoles","volume":"10","author":"Kaminskyy","year":"2011","journal-title":"Synlett"},{"key":"10.1016\/j.ejmech.2023.115304_bib79","series-title":"Version 1.171.41.93a","author":"CrysAlis","year":"2020"},{"key":"10.1016\/j.ejmech.2023.115304_bib80","first-page":"3","article-title":"SHELXT - integrated space-group and crystal-structure determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr."},{"key":"10.1016\/j.ejmech.2023.115304_bib81","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr."},{"key":"10.1016\/j.ejmech.2023.115304_bib82","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","article-title":"WinGX and ORTEP for windows: an update","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Crystallogr."},{"key":"10.1016\/j.ejmech.2023.115304_bib83","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. Crystallogr."},{"issue":"14","key":"10.1016\/j.ejmech.2023.115304_bib84","doi-asserted-by":"crossref","first-page":"1639","DOI":"10.1002\/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B","article-title":"Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function","volume":"19","author":"Morris","year":"1998","journal-title":"J. Comput. Chem."},{"issue":"2","key":"10.1016\/j.ejmech.2023.115304_bib85","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1006\/jmbi.1994.1017","article-title":"Significance of root-mean-square deviation in comparing three-dimensional structures of globular proteins","volume":"235","author":"Maiorov","year":"1994","journal-title":"J. Mol. Biol."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib86","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1515\/labmed-2019-0098","article-title":"A colorimetric method to measure oxidized, reduced and total glutathione levels in erythrocytes","volume":"43","author":"Alisik","year":"2019","journal-title":"J. Lab. Med."},{"key":"10.1016\/j.ejmech.2023.115304_bib87","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2022.114422","article-title":"Novel hybrid pyrrolidinedione-thiazolidinones as potential anticancer agents: synthesis and biological evaluation","volume":"238","author":"Finiuk","year":"2022","journal-title":"Eur. J. Med. Chem."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib88","doi-asserted-by":"crossref","first-page":"2315","DOI":"10.1038\/nprot.2006.339","article-title":"Clonogenic assay of cells in vitro","volume":"1","author":"Franken","year":"2006","journal-title":"Nat. Protoc."},{"issue":"1","key":"10.1016\/j.ejmech.2023.115304_bib89","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1097\/CAD.0000000000000686","article-title":"Proapoptotic effects of novel thiazole derivative on human glioma cells","volume":"30","author":"Finiuk","year":"2019","journal-title":"Anti Cancer Drugs"},{"key":"10.1016\/j.ejmech.2023.115304_bib90","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.ejmech.2016.05.029","article-title":"Lupane and 18\u03b1-oleanane derivatives substituted in the position 2, their cytotoxicity and influence on cancer cells","volume":"121","author":"Borkova","year":"2016","journal-title":"Eur. J. Med. Chem."},{"issue":"5","key":"10.1016\/j.ejmech.2023.115304_bib91","doi-asserted-by":"crossref","DOI":"10.1038\/cddis.2014.193","article-title":"Cab45S inhibits the ER stress-induced IRE1-JNK pathway and apoptosis via GRP78\/BiP","volume":"5","author":"Chen","year":"2014","journal-title":"Cell Death Dis."},{"issue":"19","key":"10.1016\/j.ejmech.2023.115304_bib92","doi-asserted-by":"crossref","first-page":"6219","DOI":"10.3390\/molecules27196219","article-title":"Development of novel pyridine-thiazole hybrid molecules as potential anticancer agents","volume":"27","author":"Ivasechko","year":"2022","journal-title":"Molecules"}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523423002702?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523423002702?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,4,30]],"date-time":"2026-04-30T06:03:48Z","timestamp":1777529028000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523423002702"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,4]]},"references-count":92,"alternative-id":["S0223523423002702"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2023.115304","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2023,4]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Molecular design, synthesis and anticancer activity of new thiopyrano[2,3-d]thiazoles based on 5-hydroxy-1,4-naphthoquinone (juglone)","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2023.115304","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2023 The Authors. Published by Elsevier Masson SAS.","name":"copyright","label":"Copyright"}],"article-number":"115304"}}