{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,12]],"date-time":"2026-05-12T11:17:30Z","timestamp":1778584650044,"version":"3.51.4"},"reference-count":49,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2019,8,29]],"date-time":"2019-08-29T00:00:00Z","timestamp":1567036800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100002347","name":"Bundesministerium f\u00fcr Bildung und Forschung","doi-asserted-by":"publisher","award":["FKZ 03FH025IX4"],"award-info":[{"award-number":["FKZ 03FH025IX4"]}],"id":[{"id":"10.13039\/501100002347","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2019,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Due to their high specificity and efficacy, triazoles have become versatile antifungals to treat fungal infections in human healthcare and to control phytopathogenic fungi in agriculture. However, azole resistance is an emerging problem affecting human health as well as food security. Here we describe the synthesis of 10 novel {2\u2010(3\u2010R\u20101<jats:italic>H<\/jats:italic>\u20101,2,4\u2010triazol\u20105\u2010yl)phenyl}amines. Their structure was ascertained by liquid chromatography\u2013mass spectrometry, <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C NMR, and elemental analysis data. Applying an in vitro growth assay, these triazoles show moderate to significant antifungal activity against the opportunistic pathogen <jats:italic>Aspergillus niger<\/jats:italic>, 12 fungi (<jats:italic>Fusarium oxysporum<\/jats:italic>, <jats:italic>Fusarium fujikuroi<\/jats:italic>, <jats:italic>Colletotrichum higginsianum<\/jats:italic>, <jats:italic>Gaeumannomyces graminis<\/jats:italic>, <jats:italic>Colletotrichum coccodes<\/jats:italic>, <jats:italic>Claviceps purpurea<\/jats:italic>, <jats:italic>Alternaria alternata<\/jats:italic>, <jats:italic>Mucor indicus<\/jats:italic>, <jats:italic>Fusarium graminearum<\/jats:italic>, <jats:italic>Verticillium lecanii<\/jats:italic>, <jats:italic>Botrytis cinerea<\/jats:italic>, <jats:italic>Penicillium digitatum<\/jats:italic>) and three oomycetes (<jats:italic>Phytophtora infestans<\/jats:italic> GL\u20101, <jats:italic>P. infestans<\/jats:italic> 4\/91; R+ and 4\/91; R\u2212) in the concentration range from 1 to 50\u2009\u00b5g\/ml (0.003\u20132.1\u2009\u03bcM). Frontier molecular orbital energies were determined to predict their genotoxic potential. Molecular docking calculations taking into account six common fungal enzymes point to 14\u03b1\u2010demethylase (CYP51) and <jats:italic>N<\/jats:italic>\u2010myristoyltransferase as the most probable fungal targets. With respect to effectiveness, structure\u2013activity calculations revealed the strong enhancing impact of adamantyl residues. The shown nonmutagenicity in the <jats:italic>Salmonella<\/jats:italic> reverse\u2010mutagenicity assay and no violations of drug\u2010likeness parameters suggest the good bioavailability and attractive ecotoxicological profile of the studied triazoles.<\/jats:p>","DOI":"10.1002\/ardp.201900092","type":"journal-article","created":{"date-parts":[[2019,8,29]],"date-time":"2019-08-29T08:40:38Z","timestamp":1567068038000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and mode of action studies of novel {2\u2010(3\u2010R\u20101<i>H<\/i>\u20101,2,4\u2010triazol\u20105\u2010yl)phenyl}amines to combat pathogenic fungi"],"prefix":"10.1002","volume":"352","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0057-1551","authenticated-orcid":false,"given":"Lyudmyla","family":"Antypenko","sequence":"first","affiliation":[{"name":"Department of Food and Bioproduct Technology Neubrandenburg University  Neubrandenburg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4807-9008","authenticated-orcid":false,"given":"Zhanar","family":"Sadykova","sequence":"additional","affiliation":[{"name":"Department of Food and Bioproduct Technology Neubrandenburg University  Neubrandenburg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2008-8380","authenticated-orcid":false,"given":"Kostiantyn","family":"Shabelnyk","sequence":"additional","affiliation":[{"name":"Departments of Pharmaceutical Chemistry, Organic and Bioorganic Chemistry Zaporizhzhya State Medical University  Zaporizhzhya Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fatuma","family":"Meyer","sequence":"additional","affiliation":[{"name":"Department of Food and Bioproduct Technology Neubrandenburg University  Neubrandenburg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8017-9108","authenticated-orcid":false,"given":"Sergiy","family":"Kovalenko","sequence":"additional","affiliation":[{"name":"Departments of Pharmaceutical Chemistry, Organic and Bioorganic Chemistry Zaporizhzhya State Medical University  Zaporizhzhya Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vera","family":"Meyer","sequence":"additional","affiliation":[{"name":"Department of Applied and Molecular Microbiology, Institute of Biotechnology Technische Universit\u00e4t Berlin  Berlin Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leif\u2010Alexander","family":"Garbe","sequence":"additional","affiliation":[{"name":"Department of Food and Bioproduct Technology Neubrandenburg University  Neubrandenburg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karl","family":"Steffens","sequence":"additional","affiliation":[{"name":"Department of Food and Bioproduct Technology Neubrandenburg University  Neubrandenburg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,8,29]]},"reference":[{"key":"e_1_2_9_1_2_1","doi-asserted-by":"publisher","DOI":"10.1186\/s40694-016-0024-8"},{"key":"e_1_2_9_1_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2016.11.019"},{"key":"e_1_2_9_1_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.2780150107"},{"key":"e_1_2_9_1_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12154-014-0121-1"},{"key":"e_1_2_9_1_6_1","doi-asserted-by":"publisher","DOI":"10.1042\/bj2660475"},{"key":"e_1_2_9_1_7_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1324245111"},{"key":"e_1_2_9_1_8_1","first-page":"1","volume":"1","author":"Fairlamb A. 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