{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T21:48:38Z","timestamp":1792273718588,"version":"4.4.0"},"reference-count":62,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2021,10,1]],"date-time":"2021-10-01T00:00:00Z","timestamp":1633046400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2022,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Two series comprising 20 novel benzenesulfonamides bearing thioureido\u2010linked pyrazole <jats:bold>8<\/jats:bold> and amino\u20101,2,4\u2010thiadiazole <jats:bold>10<\/jats:bold> were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor\u2010associated isoforms IX and XII. Molecular modeling studies of some potent derivatives (<jats:bold>8a<\/jats:bold>, <jats:bold>8c<\/jats:bold>, <jats:bold>10a<\/jats:bold>, and <jats:bold>10c<\/jats:bold>) were also performed against isoforms hCA I, II, and XII. Both the promising series of compounds were synthesized by using commercially available mtethyl ketones and sulfanilamide as the starting materials. Interestingly, this paper also reports a novel methodology for the synthesis of amino\u20101,2,4\u2010thiadiazoles <jats:bold>10<\/jats:bold> using 3\u2010amino isoxazoles and 4\u2010isothiocyanatobenzenesulfonamide as reactants. The activity profile of all the newly synthesized compounds reveals that amino\u2010linked 1,2,4\u2010thiadiazoles <jats:bold>10<\/jats:bold> were better inhibitors of the cytosolic isoform, hCA I, as compared to thioureido\u2010linked pyrazoles <jats:bold>8<\/jats:bold>. Further, hCA II was strongly inhibited by nearly all the newly synthesized sulfonamides, while all the compounds were less effective as hCA IX and XII inhibitors compared to the standard drug acetazolamide. However, in terms of selectivity, compound <jats:bold>8e<\/jats:bold> was found to be the most selective inhibitor of hCA II, which is the isoform associated with glaucoma, edema, altitude sickness, and epilepsy.<\/jats:p>","DOI":"10.1002\/ardp.202100241","type":"journal-article","created":{"date-parts":[[2021,10,2]],"date-time":"2021-10-02T10:02:24Z","timestamp":1633168944000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Novel benzenesulfonamide\u2010bearing pyrazoles and 1,2,4\u2010thiadiazoles as selective carbonic anhydrase inhibitors"],"prefix":"10.1002","volume":"355","author":[{"given":"Rajiv","family":"Kumar","sequence":"first","affiliation":[{"name":"Department of Chemistry Kurukshetra University  Kurukshetra India"},{"name":"Department of Chemistry Ch. Mani Ram Godara Government College for Women, Bhodia Khera  Fatehabad India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amit","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Chemistry Kurukshetra University  Kurukshetra India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sita","family":"Ram","sequence":"additional","affiliation":[{"name":"Department of Chemistry Kurukshetra University  Kurukshetra India"},{"name":"Department of Chemistry J. C. Bose University of Science and Technology, YMCA  Faridabad India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Angeli","sequence":"additional","affiliation":[{"name":"NEUROFARBA Department\u2014Pharmaceutical and Nutraceutical Section University of Florence, Polo Scientifico  Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alessandro","family":"Bonardi","sequence":"additional","affiliation":[{"name":"NEUROFARBA Department\u2014Pharmaceutical and Nutraceutical Section University of Florence, Polo Scientifico  Firenze Italy"},{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modelling Cheminformatics &amp; QSAR University of Florence, Polo Scientifico  Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alessio","family":"Nocentini","sequence":"additional","affiliation":[{"name":"NEUROFARBA Department\u2014Pharmaceutical and Nutraceutical Section University of Florence, Polo Scientifico  Firenze Italy"},{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modelling Cheminformatics &amp; QSAR University of Florence, Polo Scientifico  Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paola","family":"Gratteri","sequence":"additional","affiliation":[{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modelling Cheminformatics &amp; QSAR University of Florence, Polo Scientifico  Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"NEUROFARBA Department\u2014Pharmaceutical and Nutraceutical Section University of Florence, Polo Scientifico  Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6613-1634","authenticated-orcid":false,"given":"Pawan K.","family":"Sharma","sequence":"additional","affiliation":[{"name":"Department of Chemistry Kurukshetra University  Kurukshetra India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,10]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2018.1538980"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.21497"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.01.021"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200176r"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/metabo8020025"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201805039"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1080\/13543776.2018.1523897"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1080\/13543776.2018.1508453"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.12.028"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1517\/14728222.2014.991312"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.05.029"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.01.060"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360410001689540"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111714"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.11.093"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201800511"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.02.049"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.04.007"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2017.09.035"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2019.115048"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201300406"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201800251"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.11.067"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2019.04.026"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2015.05.096"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.10.018"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.02.023"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111598"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2018.05.013"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.200700218"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1122001"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2017.03.027"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.01.002"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.06.021"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.03.030"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.12.047"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2017.1367775"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.01.055"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111698"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2020.112219"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201900296"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1134\/S1070363219020257"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.9b00106"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.07.089"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201200355"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201501103"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.05.031"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)62326-9"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1515\/HC.2006.12.3-4.275"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1984-30809"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.14.1277"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11172-006-0029-1"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.09.028"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.05.026"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fct.2017.08.009"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444910006554"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.161301298"},{"key":"e_1_2_7_60_1","unstructured":"Schr\u00f6dinger Suite Release 2019\u20101: (a); Prime v.5.5 (b); Maestro v.11.9 (c); Epik v.4.7 (d); Impact v.8.2 (e) Macromodel v.12.3. (f) Glide v.8.2 Schr\u00f6dinger LLC New York NY 2019."},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00733"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2020.1752201"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.0c00403"}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.202100241","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ardp.202100241","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.202100241","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T04:10:33Z","timestamp":1693195833000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.202100241"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,10]]},"references-count":62,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2022,1]]}},"alternative-id":["10.1002\/ardp.202100241"],"URL":"https:\/\/doi.org\/10.1002\/ardp.202100241","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"value":"0365-6233","type":"print"},{"value":"1521-4184","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,10]]},"assertion":[{"value":"2021-07-03","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-09-13","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-10-01","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"2100241"}}