{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,10]],"date-time":"2026-03-10T20:35:04Z","timestamp":1773174904225,"version":"3.50.1"},"reference-count":29,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2016,1,1]],"date-time":"2016-01-01T00:00:00Z","timestamp":1451606400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"funder":[{"DOI":"10.13039\/501100001823","name":"Ministry of Education, Youth and Sports of the Czech Republic","doi-asserted-by":"publisher","award":["LO1204"],"award-info":[{"award-number":["LO1204"]}],"id":[{"id":"10.13039\/501100001823","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000857","name":"Loughborough University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000857","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000601","name":"De Montfort University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000601","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2016,1]]},"DOI":"10.1016\/j.ejmech.2015.11.043","type":"journal-article","created":{"date-parts":[[2015,11,30]],"date-time":"2015-11-30T12:51:46Z","timestamp":1448887906000},"page":"347-353","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":19,"special_numbering":"C","title":["Design, synthesis and antitrypanosomal activities of 2,6-disubstituted-4,5,7-trifluorobenzothiophenes"],"prefix":"10.1016","volume":"108","author":[{"given":"Avninder S.","family":"Bhambra","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mark","family":"Edgar","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mark R.J.","family":"Elsegood","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuqi","family":"Li","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"George W.","family":"Weaver","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Randolph R.J.","family":"Arroo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vanessa","family":"Yardley","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hollie","family":"Burrell-Saward","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vladimir","family":"Krystof","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2015.11.043_bib1","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1007\/s40262-014-0136-3","article-title":"Determination of an optimal dosing regimen for fexinidazole, a novel oral drug for the treatment of Human African Trypanosomiasis: first-in-human studies","volume":"53","author":"Tarral","year":"2014","journal-title":"Clin. Pharmacokinet."},{"key":"10.1016\/j.ejmech.2015.11.043_bib2","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1016\/j.ejmech.2015.08.042","article-title":"3-Nitrotriazole-based piperazides as potent antitrypanosomal agents","volume":"103","author":"Papadopoulou","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib3","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.ejmech.2015.05.044","article-title":"Structure-activity relationship of hybrids of cinchona alkaloids and bile acids with in\u00a0vitro antiplasmodial and antitrypanosomal activities","volume":"100","author":"Leverrier","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib4","series-title":"Scaffold-based Drug Discovery in Structure-based Drug Discovery","first-page":"129","author":"Zhang","year":"2007"},{"key":"10.1016\/j.ejmech.2015.11.043_bib5","doi-asserted-by":"crossref","first-page":"7208","DOI":"10.1021\/jo0508696","article-title":"Tetrahydropyrido[3,4-b]pyrazine scaffolds from pentafluoropyridine","volume":"70","author":"Sandford","year":"2005","journal-title":"J.\u00a0Org. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib6","doi-asserted-by":"crossref","first-page":"5040","DOI":"10.1021\/ol502381e","article-title":"Direct synthesis of diverse 2-aminobenzo[b]thiophenes via palladium-catalyzed carbon\u2013sulfur bond formation using Na2S2O3 as the sulfur source","volume":"16","author":"Hou","year":"2014","journal-title":"Org. Lett."},{"key":"10.1016\/j.ejmech.2015.11.043_bib7","doi-asserted-by":"crossref","first-page":"3034","DOI":"10.1016\/j.bmcl.2006.02.049","article-title":"New hiv-1 reverse transcriptase inhibitors based on a tricyclic benzothiophene scaffold: synthesis, resolution, and inhibitory activity","volume":"16","author":"Krajewski","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib8","doi-asserted-by":"crossref","first-page":"2273","DOI":"10.1021\/jm070050f","article-title":"Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization","volume":"50","author":"Romagnoli","year":"2007","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib9","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/j.ejmech.2014.09.045","article-title":"Novel nitro(triazole\/imidazole)-based heteroarylamides\/sulfonamides as potential antitrypanosomal agents","volume":"87","author":"Papadopoulou","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib10","doi-asserted-by":"crossref","first-page":"3472","DOI":"10.3390\/md11093472","article-title":"Discovery and evaluation of thiazinoquinones as anti-protozoal agents","volume":"11","author":"Lam","year":"2013","journal-title":"Mar. Drugs"},{"key":"10.1016\/j.ejmech.2015.11.043_bib11","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0022-1139(97)00006-7","article-title":"The preparation and properties of polyfluoro aromatic and heteroaromatic compounds","volume":"86","author":"Brooke","year":"1997","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib12","series-title":"Fluorinated Heterocyclic Compounds","author":"Petrov","year":"2009"},{"key":"10.1016\/j.ejmech.2015.11.043_bib13","first-page":"1","article-title":"Polyfluoroheteroaromatic compounds","volume":"28","author":"Chambers","year":"1982","journal-title":"Adv. Heterocycl. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib14","series-title":"Fluorine in Organic Chemistry","author":"Chambers","year":"2004"},{"key":"10.1016\/j.ejmech.2015.11.043_bib15","series-title":"Fluorine in Pharmaceutical and Medicinal Chemistry","author":"Gourveneur","year":"2012"},{"key":"10.1016\/j.ejmech.2015.11.043_bib16","series-title":"Fluorine in Medicinal Chemistry","author":"Ojima","year":"2012"},{"key":"10.1016\/j.ejmech.2015.11.043_bib17","doi-asserted-by":"crossref","first-page":"2294","DOI":"10.1039\/c0ob00790k","article-title":"Synthesis of fluorinated fused benzofurans and benzothiophenes: smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides","volume":"9","author":"Ponce Gonz\u00e1lez","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib18","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/S0022-1139(00)81642-5","article-title":"Nucleophilic substitution of pentafluoropyridines with imidazole","volume":"43","author":"Fujii","year":"1989","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib19","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1016\/j.jfluchem.2012.05.011","article-title":"Reactions of 4-substituted tetrafluoropyridine derivatives with sulfur nucleophiles: SNAr and annelation processes","volume":"143","author":"Fox","year":"2012","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib20","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/j.jfluchem.2008.12.013","article-title":"Pentafluorobenzaldehyde and its utilizing in organic synthesis","volume":"130","author":"Pa\u017eitn\u00fd","year":"2009","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib21","doi-asserted-by":"crossref","first-page":"2615","DOI":"10.1021\/jm020017n","article-title":"Molecular properties that influence the oral bioavailability of drug candidates","volume":"45","author":"Veber","year":"2002","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib22","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1016\/j.ddtec.2004.11.007","article-title":"Lead and drug-like compounds: the rule-of-five revolution","volume":"4","author":"Lipinski","year":"2004","journal-title":"Drug Discov. Today Technol."},{"key":"10.1016\/j.ejmech.2015.11.043_bib23","unstructured":"www.molinspiration.com."},{"key":"10.1016\/j.ejmech.2015.11.043_bib24","doi-asserted-by":"crossref","first-page":"3714","DOI":"10.1021\/jm000942e","article-title":"Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties","volume":"43","author":"Ertle","year":"2000","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2015.11.043_bib25","series-title":"APEX 2 and SAINT Software for CCD Diffractometers","year":"2013"},{"key":"10.1016\/j.ejmech.2015.11.043_bib26","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A\u00a0short history of SHELX","volume":"A64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr."},{"key":"10.1016\/j.ejmech.2015.11.043_bib27","first-page":"249","article-title":"Use of intensity quotients and differences in absolute structure refinement","volume":"B69","author":"Parsons","year":"2013","journal-title":"Acta Crystallogr."},{"key":"10.1016\/j.ejmech.2015.11.043_bib28","doi-asserted-by":"crossref","first-page":"1763","DOI":"10.1007\/s00018-005-5185-1","article-title":"Antiproliferative activity of olomoucine ii, a novel 2,6,9-trisubstituted purine cyclin-dependent kinase inhibitor","volume":"62","author":"Krystof","year":"2005","journal-title":"Cell. Mol. Life Sci."},{"key":"10.1016\/j.ejmech.2015.11.043_bib29","doi-asserted-by":"crossref","first-page":"1214","DOI":"10.1080\/10426507.2012.740704","article-title":"The reaction of thioacids with \u03b1-haloketones in water: an environmentally green synthesis of thioester derivatives","volume":"188","author":"Ramazani","year":"2013","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523415303792?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523415303792?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2022,6,26]],"date-time":"2022-06-26T15:26:44Z","timestamp":1656257204000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523415303792"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,1]]},"references-count":29,"alternative-id":["S0223523415303792"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2015.11.043","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2016,1]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Design, synthesis and antitrypanosomal activities of 2,6-disubstituted-4,5,7-trifluorobenzothiophenes","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2015.11.043","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Crown copyright \u00a9 2015 Published by Elsevier Masson SAS All rights reserved.","name":"copyright","label":"Copyright"}]}}