{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T16:09:24Z","timestamp":1788538164222,"version":"build-2803163510"},"reference-count":60,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2024,4,8]],"date-time":"2024-04-08T00:00:00Z","timestamp":1712534400000},"content-version":"vor","delay-in-days":7,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Biochem &amp;amp; Molecular Tox"],"published-print":{"date-parts":[[2024,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A series of novel pyrazole\u2010dicarboxamides were synthesized from pyrazole\u20103,4\u2010dicarboxylic acid chloride and various primary and secondary sulfonamides. The structures of the new compounds were confirmed by FT\u2010IR, <jats:sup>1<\/jats:sup>H\u2010NMR, <jats:sup>13<\/jats:sup>C\u2010NMR, and HRMS. Then the inhibition effects of newly synthesized molecules on human erythrocyte hCA I and hCA II isoenzymes were investigated. <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values of the compounds were in the range of 0.024\u22120.496\u2009\u00b5M for hCA I and 0.006\u22125.441\u2009\u00b5M for hCA II. Compounds <jats:bold>7a<\/jats:bold> and <jats:bold>7i<\/jats:bold> showed nanomolar level of inhibition of hCA II, and these compounds exhibited high selectivity for this isoenzyme. Molecular docking studies were performed between the most active compounds <jats:bold>7a<\/jats:bold>, <jats:bold>7b, 7i<\/jats:bold>, and the reference inhibitor <jats:bold>AAZ<\/jats:bold> and the hCAI and hCAII to investigate the binding mechanisms between the compounds and the isozymes. These compounds showed better interactions than the <jats:bold>AAZ<\/jats:bold>. ADMET and drug\u2010likeness analyses for the compounds have shown that the compounds can be used pharmacologically in living organisms.<\/jats:p>","DOI":"10.1002\/jbt.23704","type":"journal-article","created":{"date-parts":[[2024,4,8]],"date-time":"2024-04-08T12:55:02Z","timestamp":1712580902000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis, molecular docking analysis, drug\u2010likeness evaluation, and inhibition potency of new pyrazole\u20103,4\u2010dicarboxamides incorporating sulfonamide moiety as carbonic anhydrase inhibitors"],"prefix":"10.1002","volume":"38","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2638-3922","authenticated-orcid":false,"given":"\u015e\u00fcheda","family":"\u00d6zkul","sequence":"first","affiliation":[{"name":"Department of Biochemistry, Faculty of Arts and Sciences Dumlup\u0131nar University K\u00fctahya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7556-8379","authenticated-orcid":false,"given":"Ekrem","family":"Tunca","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Arts and Sciences Dumlup\u0131nar University K\u00fctahya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2781-7278","authenticated-orcid":false,"given":"Samet","family":"Mert","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Arts and Sciences Dumlup\u0131nar University K\u00fctahya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7967-2245","authenticated-orcid":false,"given":"Alpaslan","family":"Bayrakdar","sequence":"additional","affiliation":[{"name":"Vocational School of Higher Education for Healthcare Services I\u011fd\u0131r University I\u011fd\u0131r Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6391-7121","authenticated-orcid":false,"given":"Rahmi","family":"Kas\u0131mo\u011fullar\u0131","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Arts and Sciences Dumlup\u0131nar University K\u00fctahya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,4,8]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/chemistry4030065"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25010042"},{"issue":"4","key":"e_1_2_9_4_1","first-page":"1473","volume":"5","author":"Kumar K. A.","year":"2013","journal-title":"Int. J. PharmTech Res."},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1080\/00304940903077832"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.2298\/JSC101018135K"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2020.113134"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2010.00948.x"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms141121805"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.sjbs.2015.07.005"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202000100"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lfs.2013.12.005"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2022.134553"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23010134"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2012.11.008"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.2013.778245"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jhazmat.2011.08.082"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2004.12.053"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12088-017-0689-6"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.2c07539"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apsb.2022.01.002"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/0960-894X(96)00323-X"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0308185100"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2021.127924"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1152\/physrev.2000.80.2.681"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.22306"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2021.114004"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200176r"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1042\/BCJ20160115"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202100242"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.21713"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2021.113875"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26216380"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360701626173"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.03.048"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2010.07.041"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2010.491795"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0169-409X(00)00129-0"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep42717"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b00104"},{"key":"e_1_2_9_42_1","volume-title":"The Scripps Research Institute Molecular","author":"Huey R.","year":"2012"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.2174\/1568026617666170130110827"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1093-3263(02)00164-X"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1996.0897"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm0306430"},{"issue":"2","key":"e_1_2_9_47_1","first-page":"1","volume":"1","author":"Sangma C. D.","year":"2022","journal-title":"Sci. Phytochem."},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd1549"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40484-019-0172-y"},{"key":"e_1_2_9_50_1","unstructured":"Autodock Vina on PyRx 0.8 software.\u00a02022.\u00a0https:\/\/pyrx.sourceforge.io\/"},{"key":"e_1_2_9_51_1","unstructured":"RCSB Protein Data Bank.https:\/\/www.rcsb.org\/"},{"key":"e_1_2_9_52_1","unstructured":"G. M.Morris. What is the format of a PDBQT file? 2007.https:\/\/autodock.scripps.edu\/faqs-help\/faq\/what-is-the-format-of-a-pdbqt-file."},{"key":"e_1_2_9_53_1","unstructured":"BIOVIA discovery studio visualizer. 2022.\u00a0https:\/\/discover.3ds.com\/discovery-studio-visualizer-download"},{"key":"e_1_2_9_54_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13738-022-02738-x"},{"key":"e_1_2_9_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570440516"},{"key":"e_1_2_9_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.416"},{"key":"e_1_2_9_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.arabjc.2015.05.020"},{"key":"e_1_2_9_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci500568d"},{"key":"e_1_2_9_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci400001u"},{"key":"e_1_2_9_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fct.2023.113948"},{"key":"e_1_2_9_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/masy.202200108"}],"container-title":["Journal of Biochemical and Molecular Toxicology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jbt.23704","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,6,19]],"date-time":"2024-06-19T04:30:32Z","timestamp":1718771432000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jbt.23704"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,4]]},"references-count":60,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2024,4]]}},"alternative-id":["10.1002\/jbt.23704"],"URL":"https:\/\/doi.org\/10.1002\/jbt.23704","archive":["Portico"],"relation":{},"ISSN":["1095-6670","1099-0461"],"issn-type":[{"value":"1095-6670","type":"print"},{"value":"1099-0461","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,4]]},"assertion":[{"value":"2024-01-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-03-29","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-04-08","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e23704"}}