{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,28]],"date-time":"2026-05-28T00:26:29Z","timestamp":1779927989285,"version":"3.53.1"},"reference-count":39,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2022,9,29]],"date-time":"2022-09-29T00:00:00Z","timestamp":1664409600000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2022,9,29]],"date-time":"2022-09-29T00:00:00Z","timestamp":1664409600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001799","name":"Murdoch University","doi-asserted-by":"publisher","award":["R2855\/16"],"award-info":[{"award-number":["R2855\/16"]}],"id":[{"id":"10.13039\/501100001799","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":[[2022,11,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>From four focused compound libraries based on the known anticoccidial agent robenidine, 44\u2005compounds total were synthesised and screened for antigiardial activity. All active compounds were counter\u2010screened for antibiotic and cytotoxic action. Of the analogues examined, 21\u2005displayed IC<jats:sub>50<\/jats:sub>&lt;5\u2005\u03bcM, seven with IC<jats:sub>50<\/jats:sub>&lt;1.0\u2005\u03bcM. Most active were 2,2\u2032\u2010<jats:italic>bis<\/jats:italic>{[4\u2010(trifluoromethoxy)phenyl]methylene}carbonimidic dihydrazide hydrochloride (<jats:bold>30<\/jats:bold>), 2,2\u2032\u2010<jats:italic>bis<\/jats:italic>{[4\u2010(trifluoromethylsulfanyl)phenyl]methylene}carbonimidic dihydrazide hydrochloride (<jats:bold>32<\/jats:bold>), and 2,2\u2032\u2010bis[(2\u2010bromo\u20104,5\u2010dimethoxyphenyl)methylene]carbonimidic dihydrazide hydrochloride (<jats:bold>41<\/jats:bold>) with IC<jats:sub>50<\/jats:sub>=0.2\u2005\u03bcM. The maximal observed activity was a 5\u2005h IC<jats:sub>50<\/jats:sub> value of 0.2\u2005\u03bcM for <jats:bold>41<\/jats:bold>. The clinically used metronidazole was inactive at this timepoint at a concentration of 25\u2005\u03bcM. Robenidine off\u2010target effects at bacteria and cell line toxicity were removed. Analogue <jats:bold>41<\/jats:bold> was well tolerated in mice treated orally (100\u2005mg\/kg). Following 5\u2005h treatment with <jats:bold>41<\/jats:bold>, no Giardia regrowth was noted after 48\u2005h.<\/jats:p>","DOI":"10.1002\/cmdc.202200341","type":"journal-article","created":{"date-parts":[[2022,9,9]],"date-time":"2022-09-09T22:04:05Z","timestamp":1662761045000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Antigiardial Activity of Novel Guanidine Compounds"],"prefix":"10.1002","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5114-9134","authenticated-orcid":false,"given":"Andrew J.","family":"Stevens","sequence":"first","affiliation":[{"name":"School of Environmental &amp; Life Sciences The University of Newcastle  University Drive Callaghan NSW 2308 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1792-3242","authenticated-orcid":false,"given":"Rebecca","family":"Abraham","sequence":"additional","affiliation":[{"name":"Antimicrobial resistance and Infectious Diseases Laboratory, Harry butler Institute Murdoch University  90 South Street Murdoch WA 6150 Australia"},{"name":"School of Animal and Veterinary Sciences University of Adelaide, Roseworthy Campus  Mudla Wirra Road Roseworthy SA 5371 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7252-4693","authenticated-orcid":false,"given":"Kelly A.","family":"Young","sequence":"additional","affiliation":[{"name":"School of Environmental &amp; Life Sciences The University of Newcastle  University Drive Callaghan NSW 2308 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8401-5856","authenticated-orcid":false,"given":"Cecilia C.","family":"Russell","sequence":"additional","affiliation":[{"name":"School of Environmental &amp; Life Sciences The University of Newcastle  University Drive Callaghan NSW 2308 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3609-9316","authenticated-orcid":false,"given":"Siobhann N.","family":"McCluskey","sequence":"additional","affiliation":[{"name":"School of Environmental &amp; Life Sciences The University of Newcastle  University Drive Callaghan NSW 2308 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9560-301X","authenticated-orcid":false,"given":"Jennifer R.","family":"Baker","sequence":"additional","affiliation":[{"name":"School of Environmental &amp; Life Sciences The University of Newcastle  University Drive Callaghan NSW 2308 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7109-5460","authenticated-orcid":false,"given":"Bertha","family":"Rusdi","sequence":"additional","affiliation":[{"name":"Antimicrobial resistance and Infectious Diseases Laboratory, Harry butler Institute Murdoch University  90 South Street Murdoch WA 6150 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5312-2149","authenticated-orcid":false,"given":"Stephen W.","family":"Page","sequence":"additional","affiliation":[{"name":"Neoculi Pty Ltd.  Burwood 3125 Vic Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6046-0688","authenticated-orcid":false,"given":"Ryan","family":"O'Handley","sequence":"additional","affiliation":[{"name":"School of Animal and Veterinary Sciences University of Adelaide, Roseworthy Campus  Mudla Wirra Road Roseworthy SA 5371 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2757-7585","authenticated-orcid":false,"given":"Mark","family":"O'Dea","sequence":"additional","affiliation":[{"name":"Antimicrobial resistance and Infectious Diseases Laboratory, Harry butler Institute Murdoch University  90 South Street Murdoch WA 6150 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0950-2317","authenticated-orcid":false,"given":"Sam","family":"Abraham","sequence":"additional","affiliation":[{"name":"Antimicrobial resistance and Infectious Diseases Laboratory, Harry butler Institute Murdoch University  90 South Street Murdoch WA 6150 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7125-863X","authenticated-orcid":false,"given":"Adam","family":"McCluskey","sequence":"additional","affiliation":[{"name":"School of Environmental &amp; Life Sciences The University of Newcastle  University Drive Callaghan NSW 2308 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,9,29]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.3748\/wjg.v19.i47.8974"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-1878(199803)20:3<256::AID-BIES9>3.0.CO;2-P"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1128\/CMR.14.1.150-164.2001"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pmed.1001921"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pt.2006.02.015"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-7519(00)00127-2"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1051\/parasite\/2008153261"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1517\/14740338.2.6.529"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1383-5742(02)00007-8"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1093\/infdis\/140.6.984"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/bs.apar.2019.11.003"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2015.04.009"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.01159-06"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.01548-06"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.01675-12"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.03834-14"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0071597"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.02900-14"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbagen.2015.10.021"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.42.6.1488"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M114.553123"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2015.00544"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2009.06.001"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2010.12.012"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2015.00753"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pt.2018.04.007"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.4161\/gmic.22596"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1368-7646(03)00065-7"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2015.01208"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pntd.0005107"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpddr.2019.04.003"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01797"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mimet.2007.07.014"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1128\/CMR.15.3.329-341.2002"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja027953c"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mimet.2017.11.025"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics10030307"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0183457"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2020.01556"}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202200341","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cmdc.202200341","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202200341","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202200341","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:51:38Z","timestamp":1760287898000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.202200341"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,29]]},"references-count":39,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2022,11,4]]}},"alternative-id":["10.1002\/cmdc.202200341"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.202200341","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"value":"1860-7179","type":"print"},{"value":"1860-7187","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,9,29]]},"assertion":[{"value":"2022-06-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-09-29","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200341"}}