{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,14]],"date-time":"2026-02-14T04:12:10Z","timestamp":1771042330765,"version":"3.50.1"},"reference-count":117,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2020,3,12]],"date-time":"2020-03-12T00:00:00Z","timestamp":1583971200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004263","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Rio Grande do Sul","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004263","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2020,4,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We described here our results on the use of thiourea as a ligand in the copper catalysed azide\u2010alkyne cycloaddition (CuAAC) of 2\u2010azidobenzaldehyde with alkynes. Reactions were performed reacting 2\u2010azidobenzaldehyde with a range of terminal alkynes using 10\u2005mol\u2009% of copper iodide as a catalyst, 20\u2005mol\u2009% of thiourea as a ligand, triethylamine as base, DMSO as solvent at 100\u2009\u00b0C under nitrogen atmosphere. The corresponding 2\u2010(1<jats:italic>H<\/jats:italic>\u20101,2,3\u2010triazoyl)\u2010benzaldehydes (2\u2010TBH) were obtained in moderated to excellent yields and according our experiments, the use of thiourea decreases the formation of side products. The obtained compounds were screened for their binding affinity with multiple therapeutic targets of AD by molecular docking: \u03b2\u2010secretase (BACE), glycogen synthase kinase (GSK\u20103\u03b2) and acetylcholinesterase (AChE). The three compounds with highest affinity, <jats:bold>5\u2009a<\/jats:bold> (2\u2010(4\u2010phenyl\u20101<jats:italic>H<\/jats:italic>\u20101,2,3\u2010triazol\u20101\u2010yl)benzaldehyde), <jats:bold>5\u2009b<\/jats:bold> (2\u2010(4\u2010(<jats:italic>p<\/jats:italic>\u2010tolyl)\u20101<jats:italic>H<\/jats:italic>\u20101,2,3\u2010triazol\u20101\u2010yl)benzaldehyde), and <jats:bold>5\u2009d<\/jats:bold> (2\u2010(4\u2010(4\u2010(<jats:italic>tert<\/jats:italic>\u2010butyl)phenyl)\u20101<jats:italic>H<\/jats:italic>\u20101,2,3\u2010triazol\u20101\u2010yl)benzaldehyde) were selected and evaluated on its antioxidant effect, in view of select the most promising one to perform the in\u2005vivo validation. Due the antioxidant potential ally to the affinity with BACE, GSK\u20103\u03b2 and AChE, compound <jats:bold>5\u2009b<\/jats:bold> was evaluated in a mouse model of AD induced by intracerebroventricular injection of streptozotocin (STZ). Our results indicate that <jats:bold>5\u2009b<\/jats:bold> (1\u2005mg\/kg) treatment during 20\u2005days is able to reverse the cognitive and memory impairment induced by STZ trough the modulation of AChE activity, amyloid cascade and GSK\u20103\u03b2 expression.<\/jats:p>","DOI":"10.1002\/cmdc.201900622","type":"journal-article","created":{"date-parts":[[2020,2,3]],"date-time":"2020-02-03T13:36:10Z","timestamp":1580736970000},"page":"610-622","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Synthesis, Molecular Docking, and Preliminary Evaluation of 2\u2010(1,2,3\u2010Triazoyl)benzaldehydes As Multifunctional Agents for the Treatment of Alzheimer's Disease"],"prefix":"10.1002","volume":"15","author":[{"given":"Gabriel P.","family":"Costa","sequence":"first","affiliation":[{"name":"LASOL-CCQFA Universidade Federal de Pelotas \u2013 UFPel  P.O. Box 354 \u2013 96010-900 Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rodolfo S. M.","family":"Baldinotti","sequence":"additional","affiliation":[{"name":"Grupo de Pesquisa em Neurobiotecnologia \u2013 GPN, CDTec Universidade Federal de Pelotas  Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariana G.","family":"Fronza","sequence":"additional","affiliation":[{"name":"Grupo de Pesquisa em Neurobiotecnologia \u2013 GPN, CDTec Universidade Federal de Pelotas  Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9 Edmilson R.","family":"Nascimento","sequence":"additional","affiliation":[{"name":"LASOL-CCQFA Universidade Federal de Pelotas \u2013 UFPel  P.O. Box 354 \u2013 96010-900 Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u00cdtalo F. C.","family":"Dias","sequence":"additional","affiliation":[{"name":"LASOL-CCQFA Universidade Federal de Pelotas \u2013 UFPel  P.O. Box 354 \u2013 96010-900 Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariana Souza","family":"Sonego","sequence":"additional","affiliation":[{"name":"Grupo de Pesquisa em Oncologia Universidade Federal de Pelotas  Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fabiana K\u00f6mmling","family":"Seixas","sequence":"additional","affiliation":[{"name":"Grupo de Pesquisa em Oncologia Universidade Federal de Pelotas  Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1535-3795","authenticated-orcid":false,"given":"Tiago","family":"Collares","sequence":"additional","affiliation":[{"name":"Grupo de Pesquisa em Oncologia Universidade Federal de Pelotas  Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gelson","family":"Perin","sequence":"additional","affiliation":[{"name":"LASOL-CCQFA Universidade Federal de Pelotas \u2013 UFPel  P.O. Box 354 \u2013 96010-900 Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Raquel G.","family":"Jacob","sequence":"additional","affiliation":[{"name":"LASOL-CCQFA Universidade Federal de Pelotas \u2013 UFPel  P.O. Box 354 \u2013 96010-900 Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0494-5610","authenticated-orcid":false,"given":"Lucielli","family":"Savegnago","sequence":"additional","affiliation":[{"name":"Grupo de Pesquisa em Neurobiotecnologia \u2013 GPN, CDTec Universidade Federal de Pelotas  Pelotas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1074-0294","authenticated-orcid":false,"given":"Diego","family":"Alves","sequence":"additional","affiliation":[{"name":"LASOL-CCQFA Universidade Federal de Pelotas \u2013 UFPel  P.O. 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