{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T10:44:46Z","timestamp":1791456286060,"version":"4.3.4"},"reference-count":53,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2019,1,2]],"date-time":"2019-01-02T00:00:00Z","timestamp":1546387200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004473","name":"Sakarya \u00dcniversitesi","doi-asserted-by":"publisher","award":["2012\u201002\u201004\u2010036"],"award-info":[{"award-number":["2012\u201002\u201004\u2010036"]}],"id":[{"id":"10.13039\/501100004473","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":[[2019,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec><jats:label\/><jats:p>The synthesis, characterization, aggregation behavior, theoretical studies, and investigation of antimicrobial, antidiabetic, and anticholinergic properties of 4\u2010(2\u2010(5\u2010amino\u20104\u2010(4\u2010bromophenyl)\u20103\u2010methyl\u20101<jats:italic>H<\/jats:italic>\u2010pyrazol\u20101\u2010yl)ethoxy)phthalonitrile (<jats:bold>2<\/jats:bold>) and its soluble aminopyrazole\u2010substituted peripheral metallo (Mn, Co, and Ni)\u2010phthalocyanine complexes (<jats:bold>3<\/jats:bold>\u2013<jats:bold>5<\/jats:bold>) are reported for the first time. The synthesized compounds and phthalocyanine complexes were characterized spectroscopically. The new phthalonitrile derivative (<jats:bold>2<\/jats:bold>) and its peripheral metallophthalocyanine complexes (<jats:bold>3\u20135<\/jats:bold>) were found to be effective inhibitors of \u03b1\u2010glycosidase, acetylcholinesterase (AChE), human carbonic anhydrase I and II isoforms (hCA I and II), and butyrylcholinesterase (BChE) with <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values in the range of 1.55\u2009\u00b1\u20090.47 to 10.85\u2009\u00b1\u20093.43\u2009nM for \u03b1\u2010glycosidase, 8.44\u2009\u00b1\u20090.32 to 21.31\u2009\u00b1\u20097.91\u2009nM for hCA I, 11.73\u2009\u00b1\u20092.82 to 31.03\u2009\u00b1\u20094.81\u2009nM for hCA II, 101.62\u2009\u00b1\u200926.58 to 326.54\u2009\u00b1\u200989.67\u2009nM for AChE, and 68.68\u2009\u00b1\u200911.15 to 109.53\u2009\u00b1\u200919.55\u2009nM for BChE. This is the first study of peripherally substituted phthalocyanines containing an aminopyrazole group as potential carbonic anhydrase enzyme inhibitor. Also, the antimicrobial activities of the synthesized compounds were evaluated against six microorganisms (four bacteria and two <jats:italic>Candida<\/jats:italic> species) using the broth microdilution method. The gram\u2010positive bacteria were detected to be more sensitive than gram\u2010negative bacteria and yeasts in the synthesized compounds.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ardp.201800292","type":"journal-article","created":{"date-parts":[[2019,1,2]],"date-time":"2019-01-02T08:20:14Z","timestamp":1546417214000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":36,"title":["Aminopyrazole\u2010substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties"],"prefix":"10.1002","volume":"352","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1142-3936","authenticated-orcid":false,"given":"Emre","family":"G\u00fczel","sequence":"first","affiliation":[{"name":"Department of Chemistry Sakarya University Serdivan Sakarya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8710-2912","authenticated-orcid":false,"given":"\u00dcmit M.","family":"Ko\u00e7yi\u011fit","sequence":"additional","affiliation":[{"name":"Vocational School of Health Services Cumhuriyet University Sivas Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bar\u0131\u015f S.","family":"Arslan","sequence":"additional","affiliation":[{"name":"Department of Chemistry Sakarya University Serdivan Sakarya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mehmet","family":"Ata\u015f","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmaceutical Microbiology Cumhuriyet University Sivas Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3171-0633","authenticated-orcid":false,"given":"Parham","family":"Taslimi","sequence":"additional","affiliation":[{"name":"Faculty of Sciences, Department of Chemistry Ataturk University Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4363-3839","authenticated-orcid":false,"given":"Faik","family":"G\u00f6kalp","sequence":"additional","affiliation":[{"name":"Department of Math and Science Education K\u0131r\u0131kkale University K\u0131r\u0131kkale Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mehmet","family":"Nebio\u011flu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Sakarya University Serdivan Sakarya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0130lkay","family":"\u015ei\u015fman","sequence":"additional","affiliation":[{"name":"Department of Chemistry Sakarya University Serdivan Sakarya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0130lhami","family":"Gul\u00e7in","sequence":"additional","affiliation":[{"name":"Faculty of Sciences, Department of Chemistry Ataturk University Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,1,2]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.snb.2014.06.066"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cs4001927"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.solener.2018.09.039"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tsf.2013.10.177"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tsf.2015.11.065"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2015.10.005"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2017.07.058"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1080\/00958972.2017.1366471"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2012.12.027"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/jpp.328"},{"key":"e_1_2_6_12_1","doi-asserted-by":"crossref","first-page":"1051","DOI":"10.18596\/jotcsa.437645","volume":"5","author":"G\u00fczel E.","year":"2019","journal-title":"J. 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