{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T06:40:49Z","timestamp":1790836849781,"version":"4.1.0"},"reference-count":35,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2020,3,1]],"date-time":"2020-03-01T00:00:00Z","timestamp":1583020800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2020,3,1]],"date-time":"2020-03-01T00:00:00Z","timestamp":1583020800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"funder":[{"DOI":"10.13039\/501100004569","name":"Ministerstwo Edukacji i Nauki","doi-asserted-by":"publisher","award":["DS\/530-8457-D603-18"],"award-info":[{"award-number":["DS\/530-8457-D603-18"]}],"id":[{"id":"10.13039\/501100004569","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004569","name":"Ministerstwo Edukacji i Nauki","doi-asserted-by":"publisher","award":["DS\/530-M045-D674-18"],"award-info":[{"award-number":["DS\/530-M045-D674-18"]}],"id":[{"id":"10.13039\/501100004569","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004569","name":"Ministerstwo Edukacji i Nauki","doi-asserted-by":"publisher","award":["DS\/531-8227-D494-19"],"award-info":[{"award-number":["DS\/531-8227-D494-19"]}],"id":[{"id":"10.13039\/501100004569","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2020,3]]},"DOI":"10.1016\/j.bioorg.2020.103568","type":"journal-article","created":{"date-parts":[[2020,1,11]],"date-time":"2020-01-11T10:59:54Z","timestamp":1578740394000},"page":"103568","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":20,"special_numbering":"C","title":["Design, synthesis and biological evaluation of betulin-3-yl 2-amino-2-deoxy-\u03b2-d-glycopyranosides"],"prefix":"10.1016","volume":"96","author":[{"given":"Henryk","family":"Myszka","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daria","family":"Grzywacz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Magdalena","family":"Zdrowowicz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paulina","family":"Spisz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kamila","family":"Butowska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Janusz","family":"Rak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jacek","family":"Piosik","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maciej","family":"Ja\u015bkiewicz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wojciech","family":"Kamysz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beata","family":"Liberek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bioorg.2020.103568_b0005","series-title":"Medicinal Chemistry","author":"Thomas","year":"2007"},{"key":"10.1016\/j.bioorg.2020.103568_b0010","doi-asserted-by":"crossref","first-page":"959","DOI":"10.1016\/j.jpba.2006.09.026","article-title":"Simultaneous determination of betulin and betulinic acid in white birch bark using RP-HPLC","volume":"43","author":"Zhao","year":"2007","journal-title":"J. Pharmaceut. Biomed. Anal."},{"key":"10.1016\/j.bioorg.2020.103568_b0015","first-page":"1","article-title":"Betulin and its derivatives. Chemistry and biological activity","volume":"13","author":"Tolstikov","year":"2005","journal-title":"Chem. Sustain. Develop."},{"key":"10.1016\/j.bioorg.2020.103568_b0020","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1134\/S1068162006010031","article-title":"Biological activity and pharmacological prospects of lupane terpenoids: I. Natural lupane derivatives","author":"Tolstikova","year":"2006","journal-title":"Russ. J. Bioorg. Chem. 32"},{"key":"10.1016\/j.bioorg.2020.103568_b0025","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.canlet.2008.01.047","article-title":"Lupeol: Connotations for chemoprevention","volume":"263","author":"Chaturvedi","year":"2008","journal-title":"Cancer Lett."},{"key":"10.1016\/j.bioorg.2020.103568_b0030","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.jep.2014.11.010","article-title":"Medicinal plants of the genus Betula-Traditional uses and a phytochemical\u2013pharmacological review","volume":"159","author":"Rastogi","year":"2015","journal-title":"J. Ethnopharmacol."},{"key":"10.1016\/j.bioorg.2020.103568_b0035","first-page":"1","article-title":"Research progress in the promissing natural product-betulin","volume":"8","author":"Meng","year":"2018","journal-title":"Biomed. J. Sci. Tech. Res."},{"key":"10.1016\/j.bioorg.2020.103568_b0040","article-title":"Betulin and its derivatives as novel compounds with different pharmacological effects","author":"Amiri","year":"2019","journal-title":"Biotechnol. Adv."},{"key":"10.1016\/j.bioorg.2020.103568_b0045","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1016\/S0960-894X(99)00165-1","article-title":"Preparation of amino acid conjugates of betulinic acid with activity against human melanoma","volume":"9","author":"Jeong","year":"1999","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.103568_b0050","doi-asserted-by":"crossref","first-page":"4814","DOI":"10.1016\/j.bmcl.2009.06.046","article-title":"Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells","volume":"19","author":"Drag-Zalesinska","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.103568_b0055","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/j.biopha.2015.04.003","article-title":"The new esters derivatives of betulin and betulinic acid in epidermoid squamous carcinoma treatment \u2013 in vitro studies","volume":"72","author":"Dr\u0105g-Zalesi\u0144ska","year":"2015","journal-title":"Biomed. Pharmacother."},{"key":"10.1016\/j.bioorg.2020.103568_b0060","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1007\/s11101-010-9176-y","article-title":"Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins","volume":"10","author":"Gauthier","year":"2011","journal-title":"Phytochem. Rev."},{"key":"10.1016\/j.bioorg.2020.103568_b0065","doi-asserted-by":"crossref","first-page":"1123","DOI":"10.13005\/ojc\/280306","article-title":"Betulinic acid glycosides: a review","volume":"28","author":"Abdu","year":"2012","journal-title":"Orient. J. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0070","doi-asserted-by":"crossref","first-page":"6713","DOI":"10.1016\/j.bmc.2006.05.075","article-title":"Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents","volume":"14","author":"Gauthier","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0075","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/j.cbi.2010.02.038","article-title":"In vitro anticancer studies of \u03b1- and \u03b2-D-glucopyranose betulin anomers","volume":"185","author":"Kommera","year":"2010","journal-title":"Chem. Biol. Interact."},{"key":"10.1016\/j.bioorg.2020.103568_b0080","doi-asserted-by":"crossref","first-page":"995","DOI":"10.1016\/j.carres.2008.02.011","article-title":"Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents","volume":"343","author":"Cmoch","year":"2008","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.bioorg.2020.103568_b0085","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/S0008-6215(00)00199-3","article-title":"The synthesis of diosgenyl 2-amino-2-deoxy-\u03b2-D-glucopyranoside hydrochloride","volume":"328","author":"Bednarczyk","year":"2000","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.bioorg.2020.103568_b0090","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/S0008-6215(02)00407-X","article-title":"Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-\u03b2-D-glucopyranoside hydrochloride and its derivatives","volume":"338","author":"Myszka","year":"2003","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.bioorg.2020.103568_b0095","doi-asserted-by":"crossref","first-page":"3209","DOI":"10.1016\/j.bmc.2007.12.022","article-title":"Synthesis and cytotoxic activity of diosgenyl saponin analogues","volume":"16","author":"Kaskiw","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0100","doi-asserted-by":"crossref","first-page":"7670","DOI":"10.1016\/j.bmc.2009.09.046","article-title":"Structural analogues of diosgenyl saponins: synthesis and anticancer activity","volume":"17","author":"Kaskiw","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0105","doi-asserted-by":"crossref","first-page":"7110","DOI":"10.1016\/j.bmcl.2012.09.075","article-title":"Syntheses and structure\u2013activity relationship studies of N-substituted-\u03b2-D-glucosaminides as selective cytotoxic agents","volume":"22","author":"Wang","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.103568_b0110","doi-asserted-by":"crossref","first-page":"869","DOI":"10.3762\/bjoc.11.97","article-title":"N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-\u03b2-D-glucopyranoside; synthesis and antimicrobial activity","volume":"11","author":"Walczewska","year":"2015","journal-title":"Beilstein J. Org. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0115","doi-asserted-by":"crossref","first-page":"2310","DOI":"10.3762\/bjoc.13.227","article-title":"Diosgenyl 2-amino-2-deoxy-\u03b2-D-galactopyranoside: synthesis, derivatives and antimicrobial activity","volume":"13","author":"Myszka","year":"2017","journal-title":"Beilstein J. Org. Chem."},{"issue":"20","key":"10.1016\/j.bioorg.2020.103568_b0120","doi-asserted-by":"crossref","first-page":"114923","DOI":"10.1016\/j.bmc.2019.05.036","article-title":"N-Aminoacyl and N-hydroxyacyl derivatives of diosgenyl 2-amino-2-deoxy-\u03b2-d-glucopyranoside: synthesis, antimicrobial and hemolytic activities","volume":"27","author":"Grzywacz","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0125","doi-asserted-by":"crossref","first-page":"6144","DOI":"10.1016\/j.bmc.2007.06.033","article-title":"Synthesis and structure\u2013activity relationship study of cytotoxic germanicane- and lupane-type 3\u03b2-O-monodesmosidic saponins starting from betulin","volume":"15","author":"Thibeault","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0130","doi-asserted-by":"crossref","first-page":"2310","DOI":"10.1016\/j.bmcl.2009.02.076","article-title":"Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products","volume":"19","author":"Gauthier","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.103568_b0135","article-title":"Synthesis of lupane-type saponins containing an unusual \u03b1-d-idopyranoside fragment as potent cytotoxic agents","volume":"4089\u20134098","author":"Cmoch","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0140","doi-asserted-by":"crossref","first-page":"2717","DOI":"10.1016\/j.tet.2014.03.006","article-title":"Synthesis and structure \u2013 activity relationship study of cytotoxic lupane-type 3\u03b2-O-monodesmosidic saponins with an extended C-28 side chain","volume":"70","author":"Cmoch","year":"2014","journal-title":"Tetrahedron"},{"key":"10.1016\/j.bioorg.2020.103568_b0145","doi-asserted-by":"crossref","first-page":"2004","DOI":"10.1016\/j.tet.2015.02.008","article-title":"Synthesis and biological activity of new homolupanes and homolupane saponins","volume":"71","author":"Siodryk","year":"2015","journal-title":"Tetrahedron"},{"key":"10.1016\/j.bioorg.2020.103568_b0150","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/0165-1161(83)90010-9","article-title":"Revised methods for the salmonella mutagenicity test. Mutation research\/environmental mutagenesis and related subjects","volume":"113","author":"Maron","year":"1983","journal-title":"Mutat. Res."},{"issue":"1308","key":"10.1016\/j.bioorg.2020.103568_b0155","first-page":"2","article-title":"5-Iodo-4-thio-2\u2032-deoxyuridine as a sensitizer of X-ray induced cancer cell killing","volume":"20","author":"Makurat","year":"2019","journal-title":"Int. J. Mol. Sci."},{"key":"10.1016\/j.bioorg.2020.103568_b0160","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/S0027-5107(00)00064-6","article-title":"The Ames Salmonella\/microsome mutagenicity assay","volume":"455","author":"Mortelmans","year":"2000","journal-title":"Mutat. Res."},{"key":"10.1016\/j.bioorg.2020.103568_b0165","doi-asserted-by":"crossref","first-page":"3280","DOI":"10.1016\/j.bmc.2013.03.043","article-title":"Modulation of acridine mutagen ICR191 intercalation to DNA by methylxanthines \u2013 analysis with mathematical models","volume":"21","author":"Go\u0142u\u0144ski","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.103568_b0170","first-page":"1","article-title":"Reference method for broth dilution antifungal susceptibility testing of yeasts: approved standard \u2013 third edition","volume":"28","author":"Rex","year":"2008","journal-title":"Clin. Lab. Stand. Inst."},{"key":"10.1016\/j.bioorg.2020.103568_b0175","first-page":"1","article-title":"Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved standard \u2013 ninth edition","volume":"32","author":"Cockerill","year":"2012","journal-title":"Clin. Lab. Stand. Inst."}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206819314208?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206819314208?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,23]],"date-time":"2025-09-23T07:53:09Z","timestamp":1758613989000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0045206819314208"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3]]},"references-count":35,"alternative-id":["S0045206819314208"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2020.103568","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2020,3]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Design, synthesis and biological evaluation of betulin-3-yl 2-amino-2-deoxy-\u03b2-d-glycopyranosides","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2020.103568","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"103568"}}