{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T21:50:47Z","timestamp":1789681847240,"version":"4.0.1"},"reference-count":57,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2025,8,18]],"date-time":"2025-08-18T00:00:00Z","timestamp":1755475200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,8,18]],"date-time":"2025-08-18T00:00:00Z","timestamp":1755475200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Biochem &amp;amp; Molecular Tox"],"published-print":{"date-parts":[[2025,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    In this study, a novel series of multifunctional sulfonamide\u2010based compounds (\n                    <jats:bold>1\u20139<\/jats:bold>\n                    ) incorporating aziridine, dithiocarbamate, thiocyanate, and benzo[d]thiazole fragments were synthesized through nucleophilic substitution reactions using N\u20102,3\u2010dichloropropylbenzenesulfonamide as the key intermediate. The chemical structures of the synthesized compounds were elucidated by spectroscopic techniques including \u00b9H NMR, \u00b9\u00b3C NMR, and elemental analysis. The inhibitory potentials of the synthesized compounds were assessed against three key enzymes: human carbonic anhydrase isoforms I and II (hCA I and hCA II) and acetylcholinesterase (AChE). Among the synthesized derivatives, compound\n                    <jats:bold>3<\/jats:bold>\n                    demonstrated the highest inhibitory effect against hCA I with an K\n                    <jats:sub>i<\/jats:sub>\n                    of 49.45\u2009\u00b1\u2009\u202f9.13\u2009nM, exhibiting approximately 4.8\u2010fold stronger inhibition than acetazolamide (AZA). Similarly, compound\n                    <jats:bold>9<\/jats:bold>\n                    was the most potent inhibitor of hCA II (K\n                    <jats:sub>i<\/jats:sub>\n                    : 36.77\u2009\u00b1\u2009\u202f8.21\u2009nM), being 5.1\u2010fold more effective than AZA. In the AChE inhibition assay, both compounds\n                    <jats:bold>3<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    showed superior activity over the reference drug tacrine (TAC), with K\n                    <jats:sub>i<\/jats:sub>\n                    values of 148.67\u202f\u2009\u00b1\u2009\u202f78.78\u2009nM and 151.21\u202f\u2009\u00b1\u2009\u202f11.78\u2009nM, respectively, corresponding to 2.17\u2010fold and 2.13\u2010fold greater potency than TAC. The molecular docking studies were performed to examine the interactions between most potent compounds and proteins. These results emphasize the importance of present structural motifs for the various interactions. These findings support the rational design of multifunctional sulfonamides as promising scaffolds for the development of potent enzyme inhibitors targeting both CA and AChE\u2010related pathologies.\n                  <\/jats:p>","DOI":"10.1002\/jbt.70452","type":"journal-article","created":{"date-parts":[[2025,8,19]],"date-time":"2025-08-19T06:22:08Z","timestamp":1755584528000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Synthesis, Biological Evaluation and Molecular Docking of Novel Sulfonamide Derivatives as Dual Inhibitors of Carbonic Anhydrase Isoenzymes I\/II and Acetylcholinesterase"],"prefix":"10.1002","volume":"39","author":[{"given":"Sevgili","family":"Mammadova","sequence":"first","affiliation":[{"name":"Institute of Chemistry of Additives Ministry of Science and Education of the Republic of Azerbaijan Baku Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3216-1098","authenticated-orcid":false,"given":"Yeliz","family":"Demir","sequence":"additional","affiliation":[{"name":"Department of Pharmacy Services, Nihat Delibalta G\u00f6le Vocational High School Ardahan University Ardahan T\u00fcrkiye"},{"name":"Department of Chemistry, Faculty of Sciences Atat\u00fcrk University Erzurum T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zubeyda","family":"Israfilova","sequence":"additional","affiliation":[{"name":"Institute of Chemistry of Additives Ministry of Science and Education of the Republic of Azerbaijan Baku Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lala","family":"Zeynalova","sequence":"additional","affiliation":[{"name":"Institute of Chemistry of Additives Ministry of Science and Education of the Republic of Azerbaijan Baku Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nazar","family":"Nazarov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry of Additives Ministry of Science and Education of the Republic of Azerbaijan Baku Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Afsun","family":"Sujayev","sequence":"additional","affiliation":[{"name":"Institute of Chemistry of Additives Ministry of Science and Education of the Republic of Azerbaijan Baku Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nina","family":"Ladokhina","sequence":"additional","affiliation":[{"name":"Institute of Chemistry of Additives Ministry of Science and Education of the Republic of Azerbaijan Baku Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Du\u0161an","family":"Dimi\u0107","sequence":"additional","affiliation":[{"name":"University of Belgrade\u2010Faculty of Phyiscal Chemistry Belgrade Serbia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ilhami","family":"G\u00fcl\u00e7in","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences Atat\u00fcrk University Erzurum T\u00fcrkiye"},{"name":"Rectorate of A\u011fr\u0131 Ibrahim \u00c7e\u00e7en University A\u011fr\u0131 T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,8,18]]},"reference":[{"issue":"2","key":"e_1_2_8_2_1","first-page":"352","article-title":"Influence of Oxidants and the Environment on the Reaction of N,N\u2010Dichloro\u2010N\u2010Chlorobenzenesulfamide With Allyl Chloride","volume":"176","author":"Freidlina R. K.","year":"1967","journal-title":"Doklady Akademii Nauk SSSR"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.25135\/acg.oc101.21.04.2029"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202203653"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00922890"},{"issue":"10","key":"e_1_2_8_6_1","first-page":"1570","article-title":"Catalytic Aminohalogenation Reaction of \u03b2\u2010Nitrostyrenes With N,N\u2010Dichloro\u2010p\u2010Toluenesulfonamide Resulting in Dichlorinated Haloamides With Opposite Regiochemistry to Previous Systems","author":"Sanjun Z.","year":"2008","journal-title":"Synthesis"},{"issue":"40","key":"e_1_2_8_7_1","first-page":"7226","article-title":"Palladium\u2010Catalyzed Aziridination of Alkenes as Nitrogen Source Using N,N\u2010Dichloro\u2010N\u2010Tolylsulfonamide","volume":"62","author":"Han J.","year":"2006","journal-title":"Tetrahedron"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0600178"},{"issue":"11","key":"e_1_2_8_9_1","first-page":"1848","article-title":"Copper(I) Catalysts for Stereoselective Addition of N\u2010Chloramides to Double Bonds: Diastereoselective Radical Cyclization","volume":"68","author":"Hauger G.","year":"2003","journal-title":"Journal of Organic Chemistry"},{"issue":"23","key":"e_1_2_8_10_1","first-page":"4299","article-title":"Stereoselective Aziridination of Cyclic Allyl Alcohols Using Chloramine\u2010T","volume":"6","author":"Susannah C.","year":"2006","journal-title":"Organic and Biomolecular Chemistry"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1124\/pharmrev.124.001125"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.2478\/10004-1254-65-2014-2547"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202000375"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2024.125558"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1080\/13543776.2019.1629419"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmcr.2024.100131"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1080\/07391102.2023.2291163"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.abb.2024.110181"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.23837"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202401406"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fochx.2024.102125"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202403588"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2021.112556"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-022-10527-0"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1080\/13543776.2021.1874344"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.13958"},{"issue":"2","key":"e_1_2_8_28_1","first-page":"130","article-title":"The Evolving Role of Sulfonamides in Medicine and Drug Development: A Brief Review","volume":"7","author":"Bisharat H.","year":"2025","journal-title":"Advanced Journal of Chemistry, Section B: Natural Products and Medical Chemistry"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.indcrop.2024.120300"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/prp2.70088"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.22300"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202000496"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202400182"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.23255"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(61)90145-9"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103057"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01318a036"},{"key":"e_1_2_8_39_1","volume-title":"Gaussian 09, Revision C.01","author":"Frisch M. J.","year":"2009"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevA.38.3098"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.456153"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijbiomac.2022.05.009"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1994.1655"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1744309109036665"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21256"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21334"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.1c00203"},{"key":"e_1_2_8_49_1","unstructured":"Biovia. Discovery Studio 2016 Dassault Syst\u00e8mes. 2016."},{"issue":"3","key":"e_1_2_8_50_1","first-page":"396","article-title":"Synthesis of N\u2010\u03b2\u2010Chloroalkylaryl Sulfonamides and Their Study as Additives to Lubricating Oils","volume":"28","author":"Mamedov S. A.","year":"1988","journal-title":"Petrochemistry"},{"issue":"2","key":"e_1_2_8_51_1","first-page":"77","article-title":"Synthesis and Biological Activity of New Sulfonamides","volume":"3","author":"Mammadov S.","year":"2019","journal-title":"New Materials, Compounds and Applications"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-024-10901-0"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/bab.2534"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.202400147"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/ddr.22135"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202200325"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103004"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsps.2024.102025"}],"container-title":["Journal of Biochemical and Molecular Toxicology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jbt.70452","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/jbt.70452","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jbt.70452","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,12]],"date-time":"2026-04-12T05:58:27Z","timestamp":1775973507000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jbt.70452"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,8,18]]},"references-count":57,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2025,9]]}},"alternative-id":["10.1002\/jbt.70452"],"URL":"https:\/\/doi.org\/10.1002\/jbt.70452","archive":["Portico"],"relation":{},"ISSN":["1095-6670","1099-0461"],"issn-type":[{"value":"1095-6670","type":"print"},{"value":"1099-0461","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,8,18]]},"assertion":[{"value":"2025-06-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-09","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-18","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70452"}}