{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T15:12:36Z","timestamp":1788361956758,"version":"build-2803163510"},"reference-count":71,"publisher":"American Chemical Society (ACS)","issue":"23","license":[{"start":{"date-parts":[[2020,6,1]],"date-time":"2020-06-01T00:00:00Z","timestamp":1590969600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["SEP-82585"],"award-info":[{"award-number":["SEP-82585"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,6,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Triazoles occupy an important position in medicinal chemistry because of their various biological activities. The structural features of 1,2,3-triazoles enable them to act as a bioisostere of different functional groups such as amide, ester, carboxylic acid, and heterocycle, being capable of forming hydrogen bonds and \u03c0\u2013\u03c0 interactions or coordinate metal ions with biological targets. In this work, the synthesis of 1,2,3-triazole derivatives via copper(I)-catalyzed azide\u2013alkyne cycloaddition (CuAAC) is reported. Overexpression of 17\u03b2-hydroxysteroid dehydrogenase type 1 (17\u03b2-HSD1) is often found in breast cancer cells. Molecular similarity and docking analysis were used to evaluate the potential inhibitory activity of 1,2,3-triazoles synthesized over 17\u03b2-HSD1 for the treatment of mammary tumors. Our in silico analysis shows that compounds 4c, 4d, 4f, 4g, and 4j are good molecular scaffold candidates as 17\u03b2-HSD1 inhibitors.<\/jats:p>","DOI":"10.1021\/acsomega.0c01519","type":"journal-article","created":{"date-parts":[[2020,6,1]],"date-time":"2020-06-01T15:45:23Z","timestamp":1591026323000},"page":"14061-14068","source":"Crossref","is-referenced-by-count":18,"title":["Synthesis of 1,4-Biphenyl-triazole Derivatives as\nPossible 17\u03b2-HSD1 Inhibitors: An\n                    <i>in Silico<\/i>\n                    Study"],"prefix":"10.1021","volume":"5","author":[{"given":"Hiram","family":"Herna\u0301ndez-Lo\u0301pez","sequence":"first","affiliation":[{"name":"Universidad Auto\u0301noma de Zacatecas , , Carretera Zacatecas-Guadalajara Km 6, Ejido la Escondida s\/n , , ,","place":["Zacatecas, Zacatecas, Me\u0301xico, 98160"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6303-3107","authenticated-orcid":true,"given":"Socorro","family":"Leyva-Ramos","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de San Luis Potosi\u0301 , , Av. Manuel Nava 6 , Zona Universitaria, , ,","place":["San Luis Potosi\u0301, San Luis Potosi\u0301, Me\u0301xico, 78210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cesar Fernando","family":"Azael Go\u0301mez-Dura\u0301n","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de San Luis Potosi\u0301 , , Av. Manuel Nava 6 , Zona Universitaria, , ,","place":["San Luis Potosi\u0301, San Luis Potosi\u0301, Me\u0301xico, 78210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alberto","family":"Pedraza-Alvarez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de San Luis Potosi\u0301 , , Av. Manuel Nava 6 , Zona Universitaria, , ,","place":["San Luis Potosi\u0301, San Luis Potosi\u0301, Me\u0301xico, 78210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irving Rube\u0301n","family":"Rodri\u0301guez-Gutie\u0301rrez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de San Luis Potosi\u0301 , , Av. Manuel Nava 6 , Zona Universitaria, , ,","place":["San Luis Potosi\u0301, San Luis Potosi\u0301, Me\u0301xico, 78210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mario Alberto","family":"Leyva-Peralta","sequence":"additional","affiliation":[{"name":"Universidad de Sonora , , URN Campus Caborca. Av. Universidad e Irigoyen s\/n . , ,","place":["H. Caborca, Sonora, Me\u0301xico, 83621"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rodrigo Said","family":"Razo-Herna\u0301ndez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma del Estado de Morelos , . Av. Universidad 1001 . , ,","place":["Cuernavaca, Morelos, Me\u0301xico, 62209"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,6,1]]},"reference":[{"key":"2026090210121595500_cit1","doi-asserted-by":"publisher","first-page":"285","DOI":"10.3747\/co.25.4139","article-title":"Endocrine therapy for\nbreast cancer in the primary\ncare setting","volume":"25","author":"Awan","year":"2018","journal-title":"Curr. Oncol."},{"key":"2026090210121595500_cit2","doi-asserted-by":"publisher","first-page":"405","DOI":"10.1043\/TOJ-17-0036","article-title":"Endocrine Therapy for Early Breast Cancer: Updated\nReview","volume":"17","author":"Tremont","year":"2017","journal-title":"Ochsner J."},{"key":"2026090210121595500_cit3","doi-asserted-by":"publisher","first-page":"200","DOI":"10.1016\/j.jsbmb.2009.02.006","article-title":"Selective inhibition of 17\u03b2-hydroxysteroid\ndehydrogenase type 1 (17\u03b2HSD1) reduces estrogen responsive cell\ngrowth of T47-D breast cancer cells","volume":"114","author":"Kruchten","year":"2009","journal-title":"J. Steroid\nBiochem. Mol. Biol."},{"key":"2026090210121595500_cit4","doi-asserted-by":"publisher","first-page":"6725","DOI":"10.1021\/jm8006917","article-title":"Design,\nSynthesis, Biological Evaluation\nand Pharmacokinetics of Bis(hydroxyphenyl) substituted Azoles, Thiophenes,\nBenzenes, and Aza-Benzenes as Potent and Selective Nonsteroidal Inhibitors\nof 17\u03b2-Hydroxysteroid Dehydrogenase Type 1 (17\u03b2-HSD1)","volume":"51","author":"Bey","year":"2008","journal-title":"J. Med. Chem."},{"key":"2026090210121595500_cit5","doi-asserted-by":"publisher","first-page":"30","DOI":"10.1016\/j.bioorg.2017.01.010","article-title":"Medicinal\nattributes of 1,2,3-triazoles:\nCurrent developments","volume":"71","author":"Dheer","year":"2017","journal-title":"Bioorg. 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Chem."},{"key":"2026090210121595500_cit27","doi-asserted-by":"publisher","first-page":"2677","DOI":"10.1039\/c9gc00894b","article-title":"Highly regioselective and sustainable\nsolar click reaction:\nA new post-synthetic modified triazole organic polymer as a recyclable\nphotocatalyst for regioselective azide-alkyne cycloaddition reaction","volume":"21","author":"Yadav","year":"2019","journal-title":"Green Chem."},{"key":"2026090210121595500_cit28","doi-asserted-by":"publisher","first-page":"453","DOI":"10.1080\/14756366.2017.1423068","article-title":"Recent developments\non triazole nucleus in anticonvulsant\ncompounds: A review","volume":"33","author":"Song","year":"2018","journal-title":"J. Enzym. Inhib. Med. 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Ed."},{"key":"2026090210121595500_cit32","doi-asserted-by":"publisher","first-page":"466","DOI":"10.1002\/jlcr.3529","article-title":"A novel versatile\nprecursor suitable for 18F-radiolabeling via \u201cclick\nchemistry\u201d","volume":"60","author":"Lugato","year":"2017","journal-title":"J. Label. Compd. Radiopharm."},{"key":"2026090210121595500_cit33","doi-asserted-by":"publisher","first-page":"1900359","DOI":"10.1002\/marc.201900359","article-title":"The CuAAC: Principles,\nhomogeneous and heterogeneous catalysts, and novel developments and\napplications","volume":"41","author":"Neumann","year":"2020","journal-title":"Macromol. 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Chem."},{"key":"2026090210121595500_cit38","doi-asserted-by":"publisher","first-page":"10846","DOI":"10.1002\/slct.201903162","article-title":"Zinc (II) chloride as phase transfer\ncatalyst and as catalyst of cycloaddition azide ion to heterocumulenes\nand terminal alkynes in organic solvents","volume":"4","author":"Vorona","year":"2019","journal-title":"ChemistrySelect"},{"key":"2026090210121595500_cit39","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.ccr.2016.02.010","article-title":"Metal-catalyzed\nazide-alkyne \u201cclick\u201d reactions: Mechanistic overview\nand recent trends","volume":"316","author":"Wang","year":"2016","journal-title":"Coord. Chem. Rev."},{"key":"2026090210121595500_cit40","doi-asserted-by":"publisher","first-page":"257","DOI":"10.1080\/02678292.2018.1493755","article-title":"The synthesis\nof [1,2,3]-triazole-based\nbent core liquid crystals via microwave-mediated \u2019Click Reaction\u2019\nand their mesomorphic behaviour","volume":"46","author":"Wang","year":"2019","journal-title":"Liq. Cryst."},{"key":"2026090210121595500_cit41","doi-asserted-by":"publisher","first-page":"1443","DOI":"10.1071\/ch12255","article-title":"One-pot,\nthree-step reaction of 5-[(trimethylsilyl)ethynyl]pyrrolidin-2-one\nwith azides catalyzed by CuI: Synthesis of a novel class\nof 1,4-disubstituted 1,2,3-triazoles","volume":"65","author":"Stefani","year":"2012","journal-title":"Aust.\nJ. Chem."},{"key":"2026090210121595500_cit42","doi-asserted-by":"publisher","first-page":"5644","DOI":"10.1021\/jm050408c","article-title":"4-aryl-1,2,3-triazole:\nA novel template for a reversible methionine aminopeptidase 2 inhibitor,\noptimized to inhibit angiogenesis in vivo","volume":"48","author":"Kallander","year":"2005","journal-title":"J.\nMed. 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Chem."},{"key":"2026090210121595500_cit45","doi-asserted-by":"publisher","first-page":"3930","DOI":"10.1016\/j.bmcl.2010.05.014","article-title":"A rapid synthesis of lavendustin-mimetic small molecules\nby click fragment assembly","volume":"20","author":"Yoon","year":"2010","journal-title":"Bioorg. Med. Chem.\nLett."},{"key":"2026090210121595500_cit46","doi-asserted-by":"publisher","first-page":"3957","DOI":"10.1016\/j.bmcl.2010.04.140","article-title":"Click chemistry\nto probe Hsp90: Synthesis and evaluation\nof a series of triazole-containing novobiocin analogues","volume":"20","author":"Peterson","year":"2010","journal-title":"Bioorg. Med. Chem. 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Compd."},{"key":"2026090210121595500_cit48d","doi-asserted-by":"publisher","first-page":"1264","DOI":"10.1002\/jhet.2387","article-title":"Design and synthesis of novel triazolyl benzoxazine\nderivatives and evaluation of their antiproliferative and antibacterial\nactivity","volume":"53","author":"Khan","year":"2016","journal-title":"J. Heterocycl. Chem."},{"key":"2026090210121595500_cit48e","doi-asserted-by":"publisher","first-page":"100","DOI":"10.1007\/bf01044195","article-title":"Einwirkung\naromatischer diazoniumsalze auf ungesa\u0308ttigte verbindungen","volume":"82","author":"Brunner","year":"1951","journal-title":"Monatsh. Chem. Verw. 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Natl. Acad. Sci. U.S.A."},{"key":"2026090210121595500_cit55","doi-asserted-by":"publisher","first-page":"772","DOI":"10.1107\/s2053230x16014230","article-title":"Crystal\nstructure of rofecoxib bound to human cyclooxygenase-2","volume":"72","author":"Orlando","year":"2016","journal-title":"Acta Crystallogr., Sect. F: Struct. Biol. Commun."},{"key":"2026090210121595500_cit56","doi-asserted-by":"publisher","first-page":"288","DOI":"10.1002\/prot.20035","article-title":"GEMDOCK: A generic evolutionary method\nfor molecular\ndocking","volume":"55","author":"Yang","year":"2004","journal-title":"Proteins"},{"key":"2026090210121595500_cit57","doi-asserted-by":"publisher","first-page":"3315","DOI":"10.1021\/jm051197e","article-title":"MolDock: A New Technique for High-Accuracy Molecular\nDocking","volume":"49","author":"Thomsen","year":"2006","journal-title":"J. Med. Chem."},{"key":"2026090210121595500_cit58","unstructured":"Spartan\u201914; Wavefunction\nInc., 2014. Available from www.wavefun.com."},{"key":"2026090210121595500_cit59","doi-asserted-by":"publisher","first-page":"490","DOI":"10.1002\/(sici)1096-987x(199604)17:5\/6&lt;490::aid-jcc1&gt;3.0.co;2-p","article-title":"Merck molecular\nforce field. I. Basis, form, scope, parameterization, and performance\nof MMFF94","volume":"17","author":"Halgren","year":"1996","journal-title":"J. Comput. Chem."},{"key":"2026090210121595500_cit60","doi-asserted-by":"publisher","first-page":"1173","DOI":"10.1007\/s00894-007-0233-4","article-title":"Optimization\nof parameters for semiempirical methods V: Modification of NDDO approximations\nand application to 70 elements","volume":"13","author":"Stewart","year":"2007","journal-title":"J. Mol. Model."},{"key":"2026090210121595500_cit61","doi-asserted-by":"publisher","first-page":"169","DOI":"10.1016\/j.crci.2016.05.015","article-title":"In silico\nreceptor-based drug design of X,Y-benzenesulfonamide derivatives as\nselective COX-2 inhibitors","volume":"20","author":"Pe\u0301rez","year":"2017","journal-title":"Compt. 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