{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,19]],"date-time":"2026-10-19T09:53:28Z","timestamp":1792403608147,"version":"4.4.0"},"reference-count":36,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2016,10,1]],"date-time":"2016-10-01T00:00:00Z","timestamp":1475280000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"funder":[{"DOI":"10.13039\/501100004410","name":"Scientific and Technological Research Council of Turkey","doi-asserted-by":"publisher","award":["112S596"],"award-info":[{"award-number":["112S596"]}],"id":[{"id":"10.13039\/501100004410","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":[[2016,10]]},"DOI":"10.1016\/j.ejmech.2016.07.004","type":"journal-article","created":{"date-parts":[[2016,7,6]],"date-time":"2016-07-06T04:37:55Z","timestamp":1467779875000},"page":"510-519","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":14,"special_numbering":"C","title":["Synthesis and biological evaluation of C(5)-substituted derivatives of leukotriene biosynthesis inhibitor BRP-7"],"prefix":"10.1016","volume":"122","author":[{"given":"Serkan","family":"Levent","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jana","family":"Gerstmeier","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdurrahman","family":"Olga\u00e7","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felix","family":"Nikels","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ulrike","family":"Garscha","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Carotti","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Macchiarulo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oliver","family":"Werz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Erden","family":"Banoglu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2391-5644","authenticated-orcid":false,"given":"Burcu","family":"\u00c7al\u0131\u015fkan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2016.07.004_bib1","doi-asserted-by":"crossref","first-page":"5866","DOI":"10.1021\/cr200246d","article-title":"Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease","volume":"111","author":"Haeggstrom","year":"2011","journal-title":"Chem. Rev."},{"key":"10.1016\/j.ejmech.2016.07.004_bib2","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1016\/j.bbalip.2014.08.012","article-title":"5-Lipoxygenase, a key enzyme for leukotriene biosynthesis in health and disease","volume":"1851","author":"Radmark","year":"2015","journal-title":"Biochim. Biophys. Acta"},{"key":"10.1016\/j.ejmech.2016.07.004_bib3","doi-asserted-by":"crossref","first-page":"23","DOI":"10.2174\/1568010023344959","article-title":"5-lipoxygenase: cellular biology and molecular pharmacology","volume":"1","author":"Werz","year":"2002","journal-title":"Curr. Drug Targets Inflamm. Allergy"},{"issue":"1","key":"10.1016\/j.ejmech.2016.07.004_bib4","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1096\/fj.15-278010","article-title":"Time-resolved in situ assembly of the leukotriene-synthetic 5-lipoxygenase\/5-lipoxygenase-activating protein complex in blood leukocytes","volume":"30","author":"Gerstmeier","year":"2016","journal-title":"FASEB J."},{"key":"10.1016\/j.ejmech.2016.07.004_bib5","first-page":"1163","article-title":"FLAP inhibitors for the treatment of inflammatory diseases","volume":"10","author":"Sampson","year":"2009","journal-title":"Curr. Opin. Investig. Drugs"},{"key":"10.1016\/j.ejmech.2016.07.004_bib6","doi-asserted-by":"crossref","first-page":"858","DOI":"10.1177\/106002809603000725","article-title":"Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma","volume":"30","author":"Wenzel","year":"1996","journal-title":"Ann. Pharmacother."},{"key":"10.1016\/j.ejmech.2016.07.004_bib7","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1021\/ml100029k","article-title":"The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor","volume":"1","author":"Ducharme","year":"2010","journal-title":"ACS Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2016.07.004_bib8","doi-asserted-by":"crossref","first-page":"5803","DOI":"10.1021\/jm900945d","article-title":"5-lipoxygenase-activating protein inhibitors: development of 3-[3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (AM103)","volume":"52","author":"Hutchinson","year":"2009","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib9","doi-asserted-by":"crossref","first-page":"897","DOI":"10.1021\/jm501531v","article-title":"Discovery of AZD6642, an inhibitor of 5-lipoxygenase activating protein (FLAP) for the treatment of inflammatory diseases","volume":"58","author":"Lemurell","year":"2015","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib10","doi-asserted-by":"crossref","first-page":"1669","DOI":"10.1021\/jm501185j","volume":"58","author":"Takahashi","year":"2015","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib11","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1007\/s11883-008-0038-7","article-title":"Inflammatory signaling through leukotriene receptors in atherosclerosis","volume":"10","author":"Back","year":"2008","journal-title":"Curr. Atheroscler. Rep."},{"key":"10.1016\/j.ejmech.2016.07.004_bib12","doi-asserted-by":"crossref","first-page":"3116","DOI":"10.2174\/138161209789058020","article-title":"Inhibitors of the 5-lipoxygenase pathway in atherosclerosis","volume":"15","author":"Back","year":"2009","journal-title":"Curr. Pharm. Des."},{"key":"10.1016\/j.ejmech.2016.07.004_bib13","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1007\/s10557-008-6140-9","article-title":"Leukotriene signaling in atherosclerosis and ischemia","volume":"23","author":"Back","year":"2009","journal-title":"Cardiovasc. Drugs Ther."},{"key":"10.1016\/j.ejmech.2016.07.004_bib14","doi-asserted-by":"crossref","first-page":"946","DOI":"10.1161\/01.RES.0000264498.60702.0d","article-title":"5-Lipoxygenase-activating protein: a potential link between innate and adaptive immunity in atherosclerosis and adipose tissue inflammation","volume":"100","author":"Back","year":"2007","journal-title":"Circ. Res."},{"key":"10.1016\/j.ejmech.2016.07.004_bib15","doi-asserted-by":"crossref","first-page":"1879","DOI":"10.1517\/13543784.16.12.1879","article-title":"The potential link between atherosclerosis and the 5-lipoxygenase pathway: investigational agents with new implications for the cardiovascular field","volume":"16","author":"Whatling","year":"2007","journal-title":"Expert. Opin. Investig. Drugs"},{"key":"10.1016\/j.ejmech.2016.07.004_bib16","doi-asserted-by":"crossref","first-page":"3728","DOI":"10.1016\/j.bmc.2012.04.048","article-title":"Identification of novel benzimidazole derivatives as inhibitors of leukotriene biosynthesis by virtual screening targeting 5-lipoxygenase-activating protein (FLAP)","volume":"20","author":"Banoglu","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib17","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ejmech.2016.02.027","article-title":"4,5-Diarylisoxazol-3-carboxylic acids: a new class of leukotriene biosynthesis inhibitors potentially targeting 5-lipoxygenase-activating protein (FLAP)","volume":"113","author":"Banoglu","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib18","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1517\/17460441.2013.735228","article-title":"Overview of recent drug discovery approaches for new generation leukotriene A4 hydrolase inhibitors","volume":"8","author":"Caliskan","year":"2013","journal-title":"Expert Opin. Drug Discov."},{"key":"10.1016\/j.ejmech.2016.07.004_bib19","doi-asserted-by":"crossref","first-page":"5021","DOI":"10.1016\/j.ejmech.2011.08.009","article-title":"Pyrazol-3-propanoic acid derivatives as novel inhibitors of leukotriene biosynthesis in human neutrophils","volume":"46","author":"Caliskan","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib20","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1002\/minf.201100101","article-title":"From molecular docking to 3D-quantitative structure-activity relationships (3D-QSAR): insights into the binding mode of 5-lipoxygenase inhibitors","volume":"31","author":"Eren","year":"2012","journal-title":"Mol. Inf."},{"key":"10.1016\/j.ejmech.2016.07.004_bib21","first-page":"497","article-title":"Synthesis of 1,5-diarylpyrazol-3-propanoic acids towards inhibition of cyclooxygenase-1\/2 activity and 5-lipoxygenase-mediated LTB4 formation","volume":"60","author":"Ergun","year":"2010","journal-title":"Arzneimittelforschung"},{"key":"10.1016\/j.ejmech.2016.07.004_bib22","doi-asserted-by":"crossref","first-page":"3051","DOI":"10.1111\/bph.12625","article-title":"The novel benzimidazole derivative BRP-7 inhibits leukotriene biosynthesis in\u00a0vitro and in\u00a0vivo by targeting 5-lipoxygenase-activating protein (FLAP)","volume":"171","author":"Pergola","year":"2014","journal-title":"Br. J. Pharmacol."},{"key":"10.1016\/j.ejmech.2016.07.004_bib23","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.jpba.2013.10.039","article-title":"Chromatographic separation and biological evaluation of benzimidazole derivative enantiomers as inhibitors of leukotriene biosynthesis","volume":"89","author":"Sardella","year":"2014","journal-title":"J.\u00a0Pharm. Biomed. Anal."},{"key":"10.1016\/j.ejmech.2016.07.004_bib24","doi-asserted-by":"crossref","first-page":"7902","DOI":"10.1021\/jm100762r","article-title":"Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore","volume":"53","author":"Fleming","year":"2010","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib25","doi-asserted-by":"crossref","first-page":"3377","DOI":"10.1096\/fj.11-182758","article-title":"Testosterone suppresses phospholipase D, causing sex differences in leukotriene biosynthesis in human monocytes","volume":"25","author":"Pergola","year":"2011","journal-title":"FASEB J."},{"key":"10.1016\/j.ejmech.2016.07.004_bib26","doi-asserted-by":"crossref","first-page":"1347","DOI":"10.1084\/jem.178.4.1347","article-title":"Lipopolysaccharides prime whole human blood and isolated neutrophils for the increased synthesis of 5-lipoxygenase products by enhancing arachidonic acid availability: involvement of the CD14 antigen","volume":"178","author":"Surette","year":"1993","journal-title":"J.\u00a0Exp. Med."},{"key":"10.1016\/j.ejmech.2016.07.004_bib27","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1038\/sj.bjp.0707416","article-title":"The molecular mechanism of the inhibition by licofelone of the biosynthesis of 5-lipoxygenase products","volume":"152","author":"Fischer","year":"2007","journal-title":"Br. J. Pharmacol."},{"key":"10.1016\/j.ejmech.2016.07.004_bib28","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1074\/jbc.M506513200","article-title":"Arachidonic acid regulates the translocation of 5-lipoxygenase to the nuclear membranes in human neutrophils","volume":"281","author":"Flamand","year":"2006","journal-title":"J.\u00a0Biol. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib29","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1016\/j.plefa.2013.06.004","article-title":"High capacity for leukotriene biosynthesis in peripheral blood during pregnancy","volume":"89","author":"Schaible","year":"2013","journal-title":"Prostagl. Leukot. Essent. Fat. Acids"},{"key":"10.1016\/j.ejmech.2016.07.004_bib30","doi-asserted-by":"crossref","first-page":"2961","DOI":"10.1016\/j.bbagen.2014.05.016","article-title":"An experimental cell-based model for studying the cell biology and molecular pharmacology of 5-lipoxygenase-activating protein in leukotriene biosynthesis","volume":"1840","author":"Gerstmeier","year":"2014","journal-title":"Biochim. Biophys. Acta"},{"key":"10.1016\/j.ejmech.2016.07.004_bib31","doi-asserted-by":"crossref","first-page":"1436","DOI":"10.1016\/S0021-9258(19)40034-3","article-title":"MK886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore-challenged leukocytes","volume":"265","author":"Rouzer","year":"1990","journal-title":"J.\u00a0Biol. Chem."},{"key":"10.1016\/j.ejmech.2016.07.004_bib32","doi-asserted-by":"crossref","first-page":"510","DOI":"10.1126\/science.1144346","article-title":"Crystal structure of inhibitor-bound human 5-lipoxygenase-activating protein","volume":"317","author":"Ferguson","year":"2007","journal-title":"Science"},{"key":"10.1016\/j.ejmech.2016.07.004_bib33","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD: visual molecular dynamics","volume":"14","author":"Humphrey","year":"1996","journal-title":"J.\u00a0Mol. Graph. Model"},{"key":"10.1016\/j.ejmech.2016.07.004_bib34","doi-asserted-by":"crossref","first-page":"2607","DOI":"10.1016\/j.bmcl.2015.04.090","article-title":"Recent advances for FLAP inhibitors","volume":"25","author":"Pettersen","year":"2015","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2016.07.004_bib35","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1016\/S0378-4347(00)82742-5","article-title":"Separation of lipoxins and leukotrienes from human granulocytes by high-performance liquid chromatography with a Radial-Pak cartridge after extraction with an octadecyl reversed-phase column","volume":"493","author":"Steinhilber","year":"1989","journal-title":"J.\u00a0Chromatogr."},{"key":"10.1016\/j.ejmech.2016.07.004_bib36","doi-asserted-by":"crossref","first-page":"949","DOI":"10.1096\/fj.02-0815fje","article-title":"Phosphorylation- and stimulus-dependent inhibition of cellular 5-lipoxygenase activity by nonredox-type inhibitors","volume":"17","author":"Fischer","year":"2003","journal-title":"FASEB J."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523416305517?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523416305517?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2022,7,2]],"date-time":"2022-07-02T19:28:27Z","timestamp":1656790107000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523416305517"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,10]]},"references-count":36,"alternative-id":["S0223523416305517"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2016.07.004","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2016,10]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis and biological evaluation of C(5)-substituted derivatives of leukotriene biosynthesis inhibitor BRP-7","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2016.07.004","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2016 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}