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In vitro activity against HIV and Plasmodium\nof a wide range of spiro-\u03b2-lactams and spiro-\u03b3-lactams was evaluated. Among these compounds, one\nderivative with good anti-HIV activity and two with promising antiplasmodial activity (IC50 &lt; 3.5 \u00b5M)\nwere identified.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Results:<\/jats:title>\n<jats:p>A novel synthetic route to chiral spiro-\u03b3-lactams has been established. The studied \u03b2- and \u03b3-\nlactams were not cytotoxic, and three compounds with promising antimicrobial activity were identified,\nwhose structural modulation may lead to new and more potent drugs.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Conclusion:<\/jats:title>\n<jats:p>The designed structural modulation of biologically active spiro-\u03b2-lactams involved the replacement\nof the four-membered \u03b2-lactam ring by a five-membered \u03b3-lactam ring. Although conformational\nand superimposition computational studies revealed no significant differences between \u03b2- and \u03b3-\nlactam pharmacophoric features, the studied structural modulation did not lead to compounds with a\nsimilar biological profile. The observed results suggest that the \u03b2-lactamic core is a requirement for the\nactivity against both HIV and Plasmodium.<\/jats:p>\n<\/jats:sec>","DOI":"10.2174\/1568026619666191105110049","type":"journal-article","created":{"date-parts":[[2019,11,6]],"date-time":"2019-11-06T14:30:50Z","timestamp":1573050650000},"page":"140-152","update-policy":"https:\/\/doi.org\/10.2174\/bsp_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Spiro-Lactams as Novel Antimicrobial Agents"],"prefix":"10.2174","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2175-8796","authenticated-orcid":true,"given":"Am\u00e9rico J.S.","family":"Alves","sequence":"first","affiliation":[{"name":"CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2686-036X","authenticated-orcid":true,"given":"Nuno G.","family":"Alves","sequence":"additional","affiliation":[{"name":"CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3605-4716","authenticated-orcid":true,"given":"C\u00e1tia C.","family":"Carat\u00e3o","sequence":"additional","affiliation":[{"name":"CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6645-2198","authenticated-orcid":true,"given":"Margarida I.M.","family":"Esteves","sequence":"additional","affiliation":[{"name":"CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0046-648X","authenticated-orcid":true,"given":"Diana","family":"Fontinha","sequence":"additional","affiliation":[{"name":"Instituto de Medicina Molecular Joao Lobo Antunes, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2022-8921","authenticated-orcid":true,"given":"In\u00eas","family":"B\u00e1rtolo","sequence":"additional","affiliation":[{"name":"Instituto de Investigacao do Medicamento (iMed.ULisboa), Faculdade de Farmacia, Universidade de Lisboa, Av. 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