{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,3]],"date-time":"2026-06-03T15:19:13Z","timestamp":1780499953605,"version":"3.54.1"},"reference-count":84,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2021,5,6]],"date-time":"2021-05-06T00:00:00Z","timestamp":1620259200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005632","name":"Narodowe Centrum Bada\u0144 i Rozwoju","doi-asserted-by":"publisher","award":["Project POIR.04.01.02-00-0004\/17"],"award-info":[{"award-number":["Project POIR.04.01.02-00-0004\/17"]}],"id":[{"id":"10.13039\/501100005632","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25\u201397%). Synthesis was performed in a \u201cone-pot\u201d, two-step procedure, in the presence of organic base (Et3N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT\/NMM\/TsO\u2212) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72\u201396%). Isothiocyanate derivatives of L- and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 &gt; 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.<\/jats:p>","DOI":"10.3390\/molecules26092740","type":"journal-article","created":{"date-parts":[[2021,5,6]],"date-time":"2021-05-06T11:10:27Z","timestamp":1620299427000},"page":"2740","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Synthesis of Isothiocyanates Using DMT\/NMM\/TsO\u2212 as a New Desulfurization Reagent"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4689-1622","authenticated-orcid":false,"given":"\u0141ukasz","family":"Janczewski","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4006-6464","authenticated-orcid":false,"given":"Dorota","family":"Kr\u0119giel","sequence":"additional","affiliation":[{"name":"Department of Environmental Biotechnology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wolczanska 171\/173, 90-924 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4581-947X","authenticated-orcid":false,"given":"Beata","family":"Kolesi\u0144ska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1270\/jsbbs.64.48","article-title":"Glucosinolate metabolism, functionality and breeding for the improvement of Brassicaceae vegetables","volume":"64","author":"Ishida","year":"2014","journal-title":"Breed. Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1016\/S0031-9422(00)00316-2","article-title":"The chemical diversity and distribution of glucosinolates and isothiocyanates among plants","volume":"56","author":"Fahey","year":"2001","journal-title":"Phytochemistry"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"11430","DOI":"10.1002\/anie.201402639","article-title":"Reactivity and stability of glucosinolates and their breakdown products in foods","volume":"53","author":"Hanschen","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4481","DOI":"10.1021\/jf501096x","article-title":"Glucosinolates, myrosinase hydrolysis products, and flavonols found in rocket (Eruca sativa and Diplotaxis tenuifolia)","volume":"62","author":"Bell","year":"2014","journal-title":"J. Agric. Food Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/S0009-2797(96)03745-3","article-title":"A review of mechanisms underlying anticarcinogenicity by brassica vegetables","volume":"103","author":"Verhoeven","year":"1997","journal-title":"Chem. Biol. Interact."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"e1700990","DOI":"10.1002\/mnfr.201700990","article-title":"Taste and flavor perceptions of glucosinolates, isothiocyanates, and related compounds","volume":"62","author":"Bell","year":"2018","journal-title":"Mol. Nutr. Food Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1016\/j.bbagen.2011.06.004","article-title":"Biological targets of isothiocyanates","volume":"1810","author":"Brown","year":"2011","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1007\/s11101-008-9109-1","article-title":"The \u201cmustard oil bomb\u201d: Not so easy to assemble?! Localization, expression and distribution of the components of the myrosinase enzyme system","volume":"8","author":"Kissen","year":"2009","journal-title":"Phytochem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"395","DOI":"10.1081\/DMR-100102342","article-title":"Inhibition of carcinogenesis by isothiocyanates","volume":"32","author":"Hecht","year":"2000","journal-title":"Drug Metab. Rev."},{"key":"ref_10","first-page":"233","article-title":"Curr. Isothiocyanates as cancer chemopreventive agents: Their biological activities and metabolism in rodents and humans","volume":"3","author":"Conaway","year":"2002","journal-title":"Drug Metab."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1093\/carcin\/bgr255","article-title":"The molecular basis that unifies the metabolism, cellular uptake and chemopreventive activities of dietary isothiocyanates","volume":"33","author":"Zhang","year":"2012","journal-title":"Carcinogenesis"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1833","DOI":"10.1093\/carcin\/bgs216","article-title":"Cancer chemoprevention with dietary isothiocyanates mature for clinical translational research","volume":"33","author":"Singh","year":"2012","journal-title":"Carcinogenesis"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"963","DOI":"10.2174\/1389557514666141106131909","article-title":"Isothiocyanate synthetic analogs: Biological activities, structure-activity relationships and synthetic strategies","volume":"14","author":"Milelli","year":"2014","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4005","DOI":"10.1007\/s13277-015-3391-5","article-title":"Isothiocyanates: A class of bioactive metabolites with chemopreventive potential","volume":"36","author":"Kumar","year":"2015","journal-title":"Tumor Biol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.canlet.2017.10.033","article-title":"Chemoprevention with isothiocyanates\u2014From bench to bedside","volume":"414","author":"Huber","year":"2018","journal-title":"Cancer Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2399","DOI":"10.1073\/pnas.89.6.2399","article-title":"A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure","volume":"89","author":"Zhang","year":"1992","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1105","DOI":"10.1007\/s00018-007-6484-5","article-title":"Molecular basis for chemoprevention by sulforaphane: A comprehensive review","volume":"64","author":"Juge","year":"2007","journal-title":"Cell. Mol. Life Sci."},{"key":"ref_18","first-page":"590","article-title":"Sulforaphane\u2013a possible agent in prevention and therapy of cancer","volume":"64","author":"Tomczyk","year":"2010","journal-title":"Postepy Hig. Med. Dosw."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2589","DOI":"10.1039\/C8FO00018B","article-title":"New highlights on the health-improving effects of sulforaphane","volume":"9","year":"2018","journal-title":"Food Funct."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2905","DOI":"10.2147\/DDDT.S100534","article-title":"Chemopreventive activity of sulforaphane","volume":"12","author":"Jiang","year":"2018","journal-title":"Drug Des. Devel. Ther."},{"key":"ref_21","first-page":"405","article-title":"Phenethyl isothiocyanate: A comprehensive review of anti-cancer mechanisms","volume":"1846","author":"Gupta","year":"2014","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"760","DOI":"10.1158\/1940-6207.CAPR-13-0242","article-title":"Benzyl isothiocyanate: Double trouble for breast cancer cells","volume":"6","author":"Rao","year":"2013","journal-title":"Cancer Prev. Res."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1002\/cmdc.201700619","article-title":"Design, synthesis, and evaluation of \u03c9-(isothiocyanato)alkylphosphinates and phosphine oxides as antiproliferative agents","volume":"13","author":"Janczewski","year":"2018","journal-title":"ChemMedChem"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4572","DOI":"10.1016\/j.bmcl.2011.05.113","article-title":"Synthesis and antiproliferative activity of novel \u03b1- and \u03b2-dialkoxyphosphoryl isothiocyanates","volume":"21","author":"Psurski","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1016\/j.ejmech.2014.02.036","article-title":"New enantiomeric fluorine-containing derivatives of sulforaphane: Synthesis, absolute configurations and biological activity","volume":"76","author":"Wiktorska","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"103454","DOI":"10.1016\/j.bioorg.2019.103454","article-title":"Fluoroaryl analogs of sulforaphane\u2014A group of compounds of anticancer and antimicrobial activity","volume":"94","author":"Kwiatkowska","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1099\/mic.0.082362-0","article-title":"The antibacterial properties of isothiocyanates","volume":"161","author":"Dufour","year":"2015","journal-title":"Microbiology"},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Romeo, L., Iori, R., Rollin, P., Bramanti, P., and Mazzon, E. (2018). Isothiocyanates: An overview of their antimicrobial activity against human infections. Molecules, 23.","DOI":"10.3390\/molecules23030624"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1039\/C2MD20196H","article-title":"Sulforaphane and erucin, natural isothiocyanates from broccoli, inhibit bacterial quorum sensing","volume":"4","author":"Ganin","year":"2013","journal-title":"Med. Chem. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1016\/j.lfs.2019.01.020","article-title":"New diaryl \u03c9-(isothiocyanato)alkylphosphonates and their mercapturic acids as potential antibacterial agents","volume":"219","author":"Janczewski","year":"2019","journal-title":"Life Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1111\/jam.12288","article-title":"Growth-inhibitory activity of natural and synthetic isothiocyanates against representative human microbial pathogens","volume":"115","author":"Kurepina","year":"2013","journal-title":"J. Appl. Microbiol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"40974","DOI":"10.1039\/C8RA08162J","article-title":"Synthesis and anti-glioblastoma effects of artemisinin-isothiocyanate derivatives","volume":"8","author":"Nyein","year":"2018","journal-title":"RSC Adv."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3920","DOI":"10.1039\/C3RA46849F","article-title":"A click chemistry approach to identify protein targets of cancer chemopreventive phenethyl isothiocyanate","volume":"4","author":"Fu","year":"2014","journal-title":"RSC Adv."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"5182","DOI":"10.1039\/C6CC08797C","article-title":"Competition-based, quantitative chemical proteomics in breast cancer cells identifies new target profiles for sulforaphane","volume":"53","author":"Clulow","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"462","DOI":"10.3762\/bjoc.12.48","article-title":"(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers","volume":"12","author":"Koutoulogenis","year":"2016","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"60798","DOI":"10.1039\/C4RA12944J","article-title":"A metal-free and a solvent-free synthesis of thio-amides and amides: An efficient Friedel\u2013Crafts arylation of isothiocyanates and isocyanates","volume":"4","author":"Varun","year":"2014","journal-title":"RSC Adv."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/cr00001a001","article-title":"Isothiocyanates in the chemistry of heterocycles","volume":"91","author":"Mukerjee","year":"1991","journal-title":"Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3625","DOI":"10.1055\/s-0036-1588066","article-title":"N-isocyanates, N-isothiocyanates and their masked\/blocked derivatives: Synthesis and reactivity","volume":"48","author":"Beauchemin","year":"2016","journal-title":"Synthesis"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"6073","DOI":"10.1039\/C7CC02373A","article-title":"Isothiocyanation of amines using the Langlois reagent","volume":"53","author":"Liao","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"16669","DOI":"10.1002\/anie.201710186","article-title":"Reaction of thiocarbonyl fluoride generated from difluorocarbene with amines","volume":"56","author":"Yu","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1831","DOI":"10.1021\/acs.orglett.7b00689","article-title":"Synthesis of isothiocyanates and unsymmetrical thioureas with the bench-stable solid reagent (Me4N)SCF3","volume":"19","author":"Scattolin","year":"2017","journal-title":"Org. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2106","DOI":"10.1021\/acs.orglett.9b00383","article-title":"Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines","volume":"21","author":"Zhen","year":"2019","journal-title":"Org. Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1144","DOI":"10.1039\/C8CC09190K","article-title":"Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur","volume":"55","author":"Feng","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"4874","DOI":"10.1039\/C8OB01061G","article-title":"Staudinger\/aza-Wittig reaction to access N\u03b2-protected amino alkyl isothiocyanates","volume":"16","author":"Santhosh","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.ejmech.2017.03.028","article-title":"Novel phosphonate analogs of sulforaphane: Synthesis, in vitro and in vivo anticancer activity","volume":"132","author":"Psurski","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1016\/j.ejmech.2014.09.052","article-title":"Sulforaphane homologues: Enantiodivergent synthesis of both enantiomers, activation of the Nrf2 transcription factor and selective cytotoxic activity","volume":"87","author":"Elhalem","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4931","DOI":"10.1016\/j.ejmech.2009.08.005","article-title":"Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity","volume":"44","author":"Noshita","year":"2009","journal-title":"Eur. J. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"729","DOI":"10.1016\/S0223-5234(03)00141-7","article-title":"Synthesis of isothiocyanate-derived mercapturic acids","volume":"38","author":"Vermeulen","year":"2003","journal-title":"Eur. J. Med. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"729","DOI":"10.1002\/cbic.200700586","article-title":"Identification, synthesis, and enzymology of non-natural glucosinolatechemopreventive candidates","volume":"9","author":"Mays","year":"2008","journal-title":"ChemBioChem"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1021\/jm00027a021","article-title":"Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: Correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes","volume":"37","author":"Posner","year":"1994","journal-title":"J. Med. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"5626","DOI":"10.1016\/j.tet.2016.07.061","article-title":"Versatile synthesis of 2\u2032-amino-2\u2032-deoxyuridine derivatives with a 2\u2032-amino group carrying linkers possessing a reactive terminal functionality","volume":"72","author":"Gondela","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1661","DOI":"10.1016\/S0040-4039(00)98578-2","article-title":"Di-2-Pyridyl thionocarbonate. A new reagent for the preparation of isothiocyanates and carbodiimides","volume":"26","author":"Kim","year":"1985","journal-title":"Tetrahedron Lett."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2465","DOI":"10.1021\/jo00325a007","article-title":"Thiocarbonyl transfer reagent chemistry. 3. Selective displacements with formaldehyde hydrazones and other nucleophiles","volume":"46","author":"Larsen","year":"1981","journal-title":"J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2613","DOI":"10.1021\/jo00363a046","article-title":"1,1\u2019-Thiocarbonyldi-2,2\u2019-pyridone. A new useful reagent for functional group conversions under essentially neutral conditions","volume":"56","author":"Kim","year":"1986","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3969","DOI":"10.1021\/jo070246n","article-title":"Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts","volume":"72","author":"Wong","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4484","DOI":"10.1039\/C8GC02261E","article-title":"Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water","volume":"20","author":"Fu","year":"2018","journal-title":"Green Chem."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Nath, J., Ghosh, H., Yella, R., and Patel, B.K. (2009). Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts. Eur. J. Org. Chem., 1849\u20131851.","DOI":"10.1002\/ejoc.200801270"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3991","DOI":"10.1055\/s-0031-1289601","article-title":"New method for the synthesis of sulforaphane and related isothiocyanates","volume":"24","author":"Chen","year":"2011","journal-title":"Synthesis"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1021\/jo01033a524","article-title":"The modified kaluza synthesis. III. The synthesis of some aromatic isothiocyanates","volume":"29","author":"Hodgkins","year":"1964","journal-title":"J. Org. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3117","DOI":"10.1016\/j.tetlet.2008.03.045","article-title":"A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate","volume":"49","author":"Munch","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"61","DOI":"10.3762\/bjoc.8.6","article-title":"A general and facile one-pot process of isothiocyanates from amines under aqueous conditions","volume":"8","author":"Sun","year":"2012","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1746","DOI":"10.1055\/s-0037-1612303","article-title":"Synthesis of isothiocyanates: An update","volume":"51","author":"Eschliman","year":"2019","journal-title":"Synthesis"},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Janczewski, \u0141., Gajda, A., and Gajda, T. (2019). Direct, microwave-assisted synthesis of isothiocyanates. Eur. J. Org. Chem., 2528\u20132532.","DOI":"10.1002\/ejoc.201900105"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1016\/j.tetlet.2003.10.182","article-title":"Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents","volume":"45","author":"Boas","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"4693","DOI":"10.1021\/jm980118e","article-title":"Nonpeptide somatostatin agonists with sst4 selectivity:\u2009 synthesis and structure\u2212activity relationships of thioureas","volume":"41","author":"Liu","year":"1998","journal-title":"J. Med. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1141","DOI":"10.1055\/s-0036-1591842","article-title":"T3P\u00ae\u2013A benign desulfurating reagent in the synthesis of isothiocyanates","volume":"50","author":"Janczewski","year":"2018","journal-title":"Synthesis"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"e1700187","DOI":"10.1002\/hlca.201700187","article-title":"4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT\/NMM\/TsO\u2212) universal coupling reagent for synthesis in solution","volume":"101","author":"Fraczyk","year":"2018","journal-title":"Helv. Chim. Acta"},{"key":"ref_68","doi-asserted-by":"crossref","unstructured":"Kolesinska, B., Rozniakowski, K.K., Fraczyk, J., Relich, I., Papini, A.M., and Kaminski, Z.J. (2015). The effect of counterion and tertiary amine on the efficiency of N-triazinylammonium sulfonates in solution and solid-phase peptide synthesis. Eur. J. Org. Chem., 401\u2013408.","DOI":"10.1002\/ejoc.201402862"},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Swiontek, M., Wasko, J., Fraczyk, J., Galecki, K., Kaminski, Z.J., and Kolesinska, B. (2019). Insulin hot-spot analogs formed with N-methylated amino acid residues inhibit aggregation of native hormone. Molecules, 24.","DOI":"10.3390\/molecules24203706"},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Ferrer, P., Roberts, I., Sydenham, E., Blackhall, K., and Shakur, H. (2009). Anti-fibrinolytic agents in post-partum haemorrhage: A systematic review. BMC Pregnancy Childbirth, 9.","DOI":"10.1186\/1471-2393-9-29"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"236","DOI":"10.2165\/00003495-198529030-00003","article-title":"Clinical application of inhibitors of fibrinolysis","volume":"29","author":"Verstraete","year":"1985","journal-title":"Drugs"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"576","DOI":"10.1093\/bja\/ael057","article-title":"Efficacy of aminocaproic, tranexamic acids in the control of bleeding during total knee replacement: A randomized clinical trial","volume":"96","author":"Camarasa","year":"2006","journal-title":"Br. J. Anaesth."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"585","DOI":"10.2165\/11209070-000000000-00000","article-title":"Tranexamic acid. A review of its use in the treatment of hyperfibrinolysis","volume":"72","author":"McCormack","year":"2012","journal-title":"Drug"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"e3054","DOI":"10.1136\/bmj.e3054","article-title":"Effect of tranexamic acid on surgical bleeding: Systematic review and cumulative meta-analysis","volume":"344","author":"Ker","year":"2012","journal-title":"BMJ"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/j.molstruc.2012.12.048","article-title":"Chiral isothiocyanates\u2013an approach to determination of the absolute configuration using circular dichroism measurement","volume":"1037","author":"Michalski","year":"2013","journal-title":"J. Mol. Struct."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1562","DOI":"10.1039\/b821335f","article-title":"Thiourea and isothiocyanate\u2013two useful chromophores for stereochemical studies. A comparison of experiment and computation","volume":"7","author":"Kwit","year":"2009","journal-title":"Org. Biomol. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"4539","DOI":"10.1021\/jo970100w","article-title":"An improved procedure for the preparation of isothiocyanates from primary amines by using hydrogen peroxide as the dehydrosulfurization reagent","volume":"62","author":"Li","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1111\/lam.12105","article-title":"Antibacterial activity and synergistic effect between watercress extracts, 2-phenylethyl isothiocyanate and antibiotics against 11 isolates of Escherichia coli from clinical and animal source","volume":"57","author":"Freitas","year":"2013","journal-title":"Lett. Appl. Microbiol."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"2036","DOI":"10.4014\/jmb.1606.06008","article-title":"Relationship between chemical structure and antimicrobial activities of isothiocyanates from cruciferous vegetables against oral pathogens","volume":"26","author":"Ko","year":"2016","journal-title":"J. Microbiol. Biotechnol."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1667","DOI":"10.1055\/s-0033-1338744","article-title":"Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process","volume":"45","author":"Li","year":"2013","journal-title":"Synthesis"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"4230","DOI":"10.1021\/acs.jmedchem.5b00035","article-title":"Methyl 3-((6-Methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)amino)benzoate (GN39482) as a tubulin polymerization inhibitor identified by morphoBase and ChemProteoBase profiling methods","volume":"58","author":"Minegishi","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"4235","DOI":"10.1021\/acs.joc.5b00403","article-title":"Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms","volume":"80","author":"Ulatowski","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"9973","DOI":"10.1002\/chem.201301493","article-title":"Enantioselective aza-michael addition of imides by using an integrated strategy involving the synthesis of a family of multifunctional catalysts, usage of multiple catalysis, and rational design of experiment","volume":"19","author":"Silvi","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"4228","DOI":"10.1021\/ol9017003","article-title":"Pd-Catalyzed cross-coupling of functionalized organozinc reagents with thiomethyl-substituted heterocycles","volume":"11","author":"Metzger","year":"2009","journal-title":"Org. Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/9\/2740\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:57:43Z","timestamp":1760162263000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/9\/2740"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,6]]},"references-count":84,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2021,5]]}},"alternative-id":["molecules26092740"],"URL":"https:\/\/doi.org\/10.3390\/molecules26092740","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,6]]}}}