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In this work, a number of compounds structurally related to <jats:bold>WC\u20109<\/jats:bold> (4\u2010phenoxyphenoxyethyl thiocyanate), a known squalene synthase inhibitor, were designed, synthesized, and evaluated for their effect on <jats:italic>T.\u2005cruzi<\/jats:italic> and <jats:italic>T.\u2005gondii<\/jats:italic> growth in tissue culture cells. Two fluorine\u2010containing derivatives, the 3\u2010(3\u2010fluorophenoxy)\u2010 and 3\u2010(4\u2010fluorophenoxy)phenoxyethyl thiocyanates, exhibited half\u2010maximal effective concentration (EC<jats:sub>50<\/jats:sub>) values of 1.6 and 4.9\u2005\u03bc<jats:sc>m<\/jats:sc>, respectively, against tachyzoites of <jats:italic>T.\u2005gondii<\/jats:italic>, whereas they showed similar potency to <jats:bold>WC\u20109<\/jats:bold> against intracellular <jats:italic>T.\u2005cruzi<\/jats:italic> (EC<jats:sub>50<\/jats:sub> values of 5.4 and 5.7\u2005\u03bc<jats:sc>m<\/jats:sc>, respectively). In addition, 2\u2010[3\u2010 (phenoxy)phenoxyethylthio]ethyl\u20101,1\u2010bisphosphonate, which is a hybrid inhibitor containing 3\u2010phenoxyphenoxy and bisphosphonate groups, has activity against <jats:italic>T.\u2005gondii<\/jats:italic> proliferation at sub\u2010micromolar levels (EC<jats:sub>50<\/jats:sub>=0.7\u2005\u03bc<jats:sc>m<\/jats:sc>), which suggests a combined inhibitory effect of the two functional groups.<\/jats:p>","DOI":"10.1002\/cmdc.201600505","type":"journal-article","created":{"date-parts":[[2016,11,25]],"date-time":"2016-11-25T05:52:47Z","timestamp":1480053167000},"page":"2690-2702","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Activity of Fluorine\u2010Containing Analogues of WC\u20109 and Structurally Related Analogues against Two Intracellular Parasites: <i>Trypanosoma cruzi<\/i> and <i>Toxoplasma gondii<\/i>"],"prefix":"10.1002","volume":"11","author":[{"given":"Mar\u00eda N.","family":"Chao","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica and UMYMFOR (CONICET-FCEyN) Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires  Pabell\u00f3n\u20052, Ciudad Universitaria C1428EHA Buenos Aires Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Catherine","family":"Li","sequence":"additional","affiliation":[{"name":"Center for Tropical and Emerging Global Diseases Department of Cellular Biology University of Georgia  Athens GA 30602 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Melissa","family":"Storey","sequence":"additional","affiliation":[{"name":"Center for Tropical and Emerging Global Diseases Department of Cellular Biology University of Georgia  Athens GA 30602 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bruno N.","family":"Falcone","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica and UMYMFOR (CONICET-FCEyN) Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires  Pabell\u00f3n\u20052, Ciudad Universitaria C1428EHA Buenos Aires Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6989-4768","authenticated-orcid":false,"given":"Sergio H.","family":"Szajnman","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica and UMYMFOR (CONICET-FCEyN) Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires  Pabell\u00f3n\u20052, Ciudad Universitaria C1428EHA Buenos Aires Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sergio M.","family":"Bonesi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica and CIHIDECAR (CONICET-FCEyN) Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires  Pabell\u00f3n\u20052, Ciudad Universitaria C1428EHA Buenos Aires Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4229-8784","authenticated-orcid":false,"given":"Roberto","family":"Docampo","sequence":"additional","affiliation":[{"name":"Center for Tropical and Emerging Global Diseases Department of Cellular Biology University of Georgia  Athens GA 30602 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Silvia N. 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