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Among the compounds currently explored, chalcones have emerged as promising bioactive scaffolds, exhibiting antiparasitic activity and the potential to inhibit key proteases, which are essential enzymes to virulence and pathogenesis of the parasite. In this study, chalcone derivatives obtained via a novel synthetic approach were evaluated for their antileishmanial activity against L.(V.)braziliensis. Their drug-likeness properties were initially assessed in silico, and the inhibitory activity against proteases was subsequently evaluated using promastigote protein extracts. In Tris\u2013HCl buffer, compound 3j exhibited the most pronounced inhibitory effect, 36% residual activity, followed by compounds 3d and 2\u2032,4\u2032,6\u2032-trimethoxy-chalcone (TMC), which showed 47% residual activity. In acetate buffer, the most effective inhibitors were 3b and 3j (34%), and 3d (35%). Cytotoxicity assays were performed in murine macrophages, and the leishmanicidal effects were evaluated against promastigotes to determine compound selectivity index (SI). TMC, 3b, 3d, 3h, and 3i exhibited SI \u2265 16.74 and were tested against intracellular amastigotes. They decreased \u226534% macrophage infection by intracellular amastigotes, and demonstrated a predictive profile for high metabolic stability with low organ toxicity risk. The findings suggest that these chalcones may act through a multitarget mechanism involving the inhibition of parasite proteases, supporting their progression to advanced stages of therapeutic validation.<\/jats:p>","DOI":"10.1021\/acsomega.6c06140","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T11:01:59Z","timestamp":1790679719000},"page":"61265-61277","source":"Crossref","is-referenced-by-count":0,"title":["Novel Synthetic\nChalcones Display Potent Anti-\n                    <i>Leishmania<\/i>\n                    (\n                    <i>Viannia<\/i>\n                    )\n                    <i>braziliensis<\/i>\n                    Profile and Inhibit\nProteolytic Activities"],"prefix":"10.1021","volume":"11","author":[{"given":"Edgar","family":"Schaeffer","sequence":"first","affiliation":[{"name":"Universidade Federal do Rio de Janeiro , , Av. Carlos Chagas Filho 373\u2500Bloco H , Cidade Universita\u0301ria, ,","place":["Rio de Janeiro, Brasil, CEP 21941-599"]},{"name":"Fundac\u0327a\u0303o Oswaldo Cruz , , Avenida Brasil 4365 , Manguinhos, ,","place":["Rio de Janeiro, Brasil, CEP 21040-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Geovane","family":"Dias-Lopes","sequence":"additional","affiliation":[{"name":"Universidade do Estado do Rio de Janeiro, UERJ , , Rua Ari\u0301zio Gomes da Costa 186 , Jardim Flamboyant, Cabo Frio, ,","place":["Rio de Janeiro, Brasil, CEP 28905-320"]},{"name":"Fundac\u0327a\u0303o Oswaldo Cruz , , Avenida Brasil 4365 , Manguinhos, ,","place":["Rio de Janeiro, Brasil, CEP 21040-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Patri\u0301cia Queiroz","family":"Monteiro","sequence":"additional","affiliation":[{"name":"Fundac\u0327a\u0303o Oswaldo Cruz , , Avenida Brasil 4365 , Manguinhos, ,","place":["Rio de Janeiro, Brasil, CEP 21040-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julia Maria","family":"Borges","sequence":"additional","affiliation":[{"name":"Fundac\u0327a\u0303o Oswaldo Cruz , , Avenida Brasil 4365 , Manguinhos, ,","place":["Rio de Janeiro, Brasil, CEP 21040-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luzia Monteiro de Castro","family":"Co\u0302rtes","sequence":"additional","affiliation":[{"name":"Fundac\u0327a\u0303o Oswaldo Cruz , , Avenida Brasil 4365 , Manguinhos, ,","place":["Rio de Janeiro, Brasil, CEP 21040-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3200-0318","authenticated-orcid":true,"given":"Alcides Jose\u0301","family":"Monteiro da Silva","sequence":"additional","affiliation":[{"name":"Universidade Federal do Rio de Janeiro , , Av. Carlos Chagas Filho 373\u2500Bloco H , Cidade Universita\u0301ria, ,","place":["Rio de Janeiro, Brasil, CEP 21941-599"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Franklin Souza da","family":"Silva","sequence":"additional","affiliation":[{"name":"Universidade Iguac\u0327u , , Avenida Abi\u0301lio Augusto Ta\u0301vora 2134 , Dom Rodrigo, Nova Iguac\u0327u, ,","place":["Rio de Janeiro, Brasil, CEP 26260-045"]},{"name":"Fundac\u0327a\u0303o Oswaldo Cruz, FIOCRUZ , , Avenida Brasil, 4036\u2500Manguinhos , ,","place":["Rio de Janeiro, Brasil, CEP 21040-361"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8703-426X","authenticated-orcid":true,"given":"Carlos Roberto","family":"Alves","sequence":"additional","affiliation":[{"name":"Fundac\u0327a\u0303o Oswaldo Cruz , , Avenida Brasil 4365 , Manguinhos, ,","place":["Rio de Janeiro, Brasil, CEP 21040-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,29]]},"reference":[{"key":"2026101315082510900_cit1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0035671","article-title":"WHO Leishmaniasis\nControl Team, Leishmaniasis worldwide and global estimates of its\nincidence","volume":"7","author":"Alvar","year":"2012","journal-title":"PLoS One"},{"key":"2026101315082510900_cit2","doi-asserted-by":"publisher","first-page":"380","DOI":"10.1111\/tmi.13210","article-title":"American tegumentary\nleishmaniasis\nin Brazil: a critical review of the current therapeutic approach with\nsystemic meglumine antimoniate and short-term possibilities for an\nalternative treatment","volume":"24","author":"Carvalho","year":"2019","journal-title":"Trop. Med. Int. Health"},{"key":"2026101315082510900_cit3","unstructured":"Pan American Health Organization.\n          .  Leishmaniasis: Epidemiological Report of\nthe Americas (No. 11); PAHO, Washington, D.C., 2022. https:\/\/www.paho.org\/en\/documents\/leishmaniasis-epidemiological-report-americas-no11-december-2022."},{"key":"2026101315082510900_cit4","doi-asserted-by":"publisher","first-page":"1573618","DOI":"10.3389\/fmolb.2025.1573618","article-title":"Unravelling drug resistance\nin leishmaniasis: genomic adaptations and emerging therapies","volume":"12","author":"Bhusal","year":"2025","journal-title":"Front. Mol. Biosci."},{"key":"2026101315082510900_cit5","doi-asserted-by":"publisher","first-page":"837460","DOI":"10.3389\/fitd.2022.837460","article-title":"Tackling drug\nresistance and other causes of treatment failure in leishmaniasis","volume":"3","author":"Wijnant","year":"2022","journal-title":"Front. Trop. Dis."},{"key":"2026101315082510900_cit6","doi-asserted-by":"publisher","first-page":"67","DOI":"10.1016\/j.exppara.2017.11.008","article-title":"Understanding serine\nproteases implications\non Leishmania spp lifecycle","volume":"184","author":"Alves","year":"2018","journal-title":"Exp. Parasitol."},{"key":"2026101315082510900_cit7","doi-asserted-by":"publisher","first-page":"1015","DOI":"10.3390\/vaccines11061015","article-title":"Degron Pathways\nand Leishmaniasis: Debating Potential Roles of Leishmania spp. Proteases Activity on Guiding Hosts Immune Response and Their\nRelevance to the Development of Vaccines","volume":"11","author":"Oliveira","year":"2023","journal-title":"Vaccines"},{"key":"2026101315082510900_cit8","doi-asserted-by":"publisher","first-page":"117500","DOI":"10.1016\/j.ejmech.2025.117500","article-title":"Targeting cysteine protease B to\ndiscover antileishmanial drugs: Directions and advances","volume":"289","author":"de Oliveira Rios","year":"2025","journal-title":"Eur. J. Med. 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Lett."},{"key":"2026101315082510900_cit12","doi-asserted-by":"publisher","first-page":"136","DOI":"10.1002\/med.20163","article-title":"Falcipain-2\ninhibitors","volume":"30","author":"Ettari","year":"2010","journal-title":"Med. Res. Rev."},{"key":"2026101315082510900_cit13","doi-asserted-by":"publisher","first-page":"114572","DOI":"10.1016\/j.ejmech.2022.114572","article-title":"Chalcone-amide,\na privileged backbone for the design and development of selective\nSARS-CoV\/SARS-CoV-2 papain-like protease inhibitors","volume":"240","author":"Valipour","year":"2022","journal-title":"Eur. J. Med. Chem."},{"key":"2026101315082510900_cit14","doi-asserted-by":"publisher","first-page":"7762","DOI":"10.1021\/acs.chemrev.7b00020","article-title":"Chalcone: A Privileged\nStructure in Medicinal Chemistry","volume":"117","author":"Zhuang","year":"2017","journal-title":"Chem. 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Chem."},{"key":"2026101315082510900_cit16","doi-asserted-by":"publisher","first-page":"3737","DOI":"10.3390\/molecules26123737","article-title":"Chalcones\nas Promising Antitumor Agents by Targeting the p53 Pathway: An Overview\nand New Insights in Drug-Likeness","volume":"26","author":"Moreira","year":"2021","journal-title":"Molecules"},{"key":"2026101315082510900_cit17","doi-asserted-by":"publisher","first-page":"2731","DOI":"10.1007\/s00436-021-07199-4","article-title":"Potential\nof Piper spp. as a source of new compounds for the leishmaniases treatment","volume":"120","author":"Peixoto","year":"2021","journal-title":"Parasitol. Res."},{"key":"2026101315082510900_cit18","doi-asserted-by":"publisher","first-page":"112784","DOI":"10.1016\/j.biopha.2022.112784","article-title":"Targeting\nchalcone binding sites in living Leishmania using a reversible fluorogenic\nbenzochalcone probe","volume":"149","author":"Batista","year":"2022","journal-title":"Biomed. Pharmacother."},{"key":"2026101315082510900_cit19","doi-asserted-by":"publisher","first-page":"2025","DOI":"10.3390\/ijms26052025","article-title":"A Virtual\nScreening Approach to Evaluate the Multitarget Potential of a Chalcone\nLibrary with Binding Properties to Oligopeptidase B and Cysteine Proteinase\nB from Leishmania (Viannia) braziliensis","volume":"26","author":"Monteiro","year":"2025","journal-title":"Int. J. Mol. Sci."},{"issue":"W1","key":"2026101315082510900_cit20","doi-asserted-by":"publisher","first-page":"W513","DOI":"10.1093\/nar\/gkae303","article-title":"ProTox 3.0:\na webserver for the prediction of toxicity of chemicals","volume":"52","author":"Banerjee","year":"2024","journal-title":"Nucleic Acids Res."},{"key":"2026101315082510900_cit21","doi-asserted-by":"publisher","first-page":"137067","DOI":"10.1016\/j.molstruc.2023.137067","article-title":"Regio-and\nchemoselective synthesis of polyaryl flavones by combination of CO\/CH\nactivation and Suzuki-Miyaura cross coupling reactions","volume":"1299","author":"Schaeffer","year":"2024","journal-title":"J. Mol. Struct."},{"key":"2026101315082510900_cit22","doi-asserted-by":"publisher","first-page":"3172","DOI":"10.1016\/j.bmcl.2016.04.096","article-title":"Synthesis\nand anti-proliferative\nactivity of fluoro-substituted chalcones","volume":"26","author":"Burmaoglu","year":"2016","journal-title":"Bioorg.\nMed. Chem. Lett."},{"key":"2026101315082510900_cit23","doi-asserted-by":"publisher","DOI":"10.1002\/047084289X.rp012","article-title":"Palladium(II)\nHydroxide on Carbon","volume-title":"Encyclopedia of Reagents\nfor Organic Synthesis","author":"King","year":"2001"},{"key":"2026101315082510900_cit24","doi-asserted-by":"publisher","first-page":"2821","DOI":"10.1016\/j.bmcl.2010.03.054","article-title":"Cytotoxicity against KB and NCI-H187 cell lines of\nmodified flavonoids from Kaempferia parviflora","volume":"20","author":"Yenjai","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026101315082510900_cit25","doi-asserted-by":"publisher","first-page":"1179","DOI":"10.1007\/s12272-009-1900-z","article-title":"Structural\nmodification of 5,7-dimethoxyflavone from Kaempferia parviflora and\nbiological activities","volume":"32","author":"Yenjai","year":"2009","journal-title":"Arch. Pharm. 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Chem."},{"key":"2026101315082510900_cit29","doi-asserted-by":"publisher","first-page":"14234","DOI":"10.1038\/s41598-021-93665-z","article-title":"Serine\nproteases profiles of Leishmania (Viannia) braziliensis clinical isolates with distinct susceptibilities to antimony","volume":"11","author":"Zabala-Pen\u0303afiel","year":"2021","journal-title":"Sci. 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Pharmacother."},{"key":"2026101315082510900_cit33","doi-asserted-by":"publisher","DOI":"10.1590\/0074-02760190111","article-title":"Antimony\nresistance in Leishmania (Viannia) braziliensis clinical isolates from atypical lesions\nassociates with increased ARM56\/ARM58 transcripts and reduced drug\nuptake","volume":"114","author":"Rugani","year":"2019","journal-title":"Mem. Inst. Oswaldo Cruz"},{"key":"2026101315082510900_cit34","doi-asserted-by":"publisher","first-page":"206","DOI":"10.1055\/s-2007-967123","article-title":"Leishmanicidal Constituents from the Leaves of Piper\nrusbyi","volume":"73","author":"Flores","year":"2007","journal-title":"Plant Med."},{"key":"2026101315082510900_cit35","doi-asserted-by":"publisher","first-page":"1234","DOI":"10.1128\/AAC.43.5.1234","article-title":"Selective Effect of 2\u2019,6\u2019-Dihydroxy-4\u2019-Methoxychalcone\nIsolated from Piper aduncum on Leishmania amazonensis","volume":"43","author":"Torres-Santos","year":"1999","journal-title":"Antimicrob. Agents Chemother."},{"key":"2026101315082510900_cit36","doi-asserted-by":"publisher","first-page":"3404","DOI":"10.1073\/pnas.051632198","article-title":"Potency of\nMichael reaction acceptors as inducers of enzymes that protect against\ncarcinogenesis depends on their reactivity with sulfhydryl groups","volume":"98","author":"Dinkova-Kostova","year":"2001","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"2026101315082510900_cit37","doi-asserted-by":"publisher","first-page":"711","DOI":"10.3109\/00498254.2012.754112","article-title":"Chemical\nreactivity and biological activity of chalcones and other \u03b1,\u03b2-unsaturated\ncarbonyl compounds","volume":"43","author":"Maydt","year":"2013","journal-title":"Xenobiotica"},{"issue":"10","key":"2026101315082510900_cit38","doi-asserted-by":"publisher","first-page":"835","DOI":"10.3390\/pathogens13100835","article-title":"Molecular\nMechanisms of Drug Resistance in Leishmania spp","volume":"13","author":"Moncada-Diaz","year":"2024","journal-title":"Pathogens"},{"issue":"9\u201310","key":"2026101315082510900_cit39","doi-asserted-by":"publisher","first-page":"495","DOI":"10.1016\/j.drudis.2013.01.008","article-title":"Shifting from the\nsingle to the multitarget paradigm in drug discovery","volume":"18","author":"Medina-Franco","year":"2013","journal-title":"Drug Discov Today"},{"key":"2026101315082510900_cit40","doi-asserted-by":"publisher","first-page":"38","DOI":"10.1016\/j.exppara.2004.10.005","article-title":"Leishmania\namazonensis: early proteinase activities during promastigote-amastigote\ndifferentiation in vitro","volume":"109","author":"Alves","year":"2005","journal-title":"Exp.\nParasitol."},{"key":"2026101315082510900_cit41","doi-asserted-by":"publisher","first-page":"1315","DOI":"10.3390\/ijms20061315","article-title":"Serine Proteinases\nin Leishmania (Viannia) braziliensis Promastigotes\nHave Distinct Subcellular Distributions and Expression","volume":"20","author":"Santos-de-Souza","year":"2019","journal-title":"Int. J. Mol. Sci."},{"key":"2026101315082510900_cit42","doi-asserted-by":"publisher","first-page":"387","DOI":"10.1186\/1756-3305-7-387","article-title":"Overview\nof the organization of protease genes in the\ngenome of Leishmania spp","volume":"7","author":"Silva-Almeida","year":"2014","journal-title":"Parasit.\nVectors"},{"key":"2026101315082510900_cit43","doi-asserted-by":"publisher","first-page":"502","DOI":"10.1016\/j.pt.2003.09.008","article-title":"Leishmaniasis-current chemotherapy\nand recent advances\nin the search for novel drugs","volume":"19","author":"Croft","year":"2003","journal-title":"Trends Parasitol."},{"key":"2026101315082510900_cit44","doi-asserted-by":"publisher","first-page":"3855","DOI":"10.1128\/AAC.00548-09","article-title":"In vitro susceptibilities\nof Leishmania donovani promastigote and amastigote\nstages to antileishmanial reference\ndrugs: practical relevance of stage-specific differences","volume":"53","author":"Vermeersch","year":"2009","journal-title":"Antimicrob. Agents Chemother."},{"key":"2026101315082510900_cit45","unstructured":"Ioset, J. R.; Brun, R.; Wenzler, T.; Kaiser, M.; Yardley, V.\n          Drug Screening\nfor Kinetoplastids Diseases: A Training Manual for Screening in Neglected\nDiseases; Drugs for Neglected Diseases\ninitiative (DNDi): Geneva, 2009. https:\/\/dndi.org\/wp-content\/uploads\/2009\/04\/kinetoplastid_drug_screening_manual_final.pdf."},{"key":"2026101315082510900_cit46","doi-asserted-by":"publisher","first-page":"751","DOI":"10.1038\/nrd4683","article-title":"Hit and lead criteria\nin drug discovery\nfor infectious diseases of the developing world","volume":"14","author":"Katsuno","year":"2015","journal-title":"Nat. Rev. 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