{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,10]],"date-time":"2026-04-10T16:53:03Z","timestamp":1775839983697,"version":"3.50.1"},"reference-count":71,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2022,4,5]],"date-time":"2022-04-05T00:00:00Z","timestamp":1649116800000},"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":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2022,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In this study, a series of new hybrid molecules containing two important functional groups on the same skeleton were designed. 4\u2010Hydroxybenzaldehyde and its two different derivatives were converted into their respective sulphonates by interacting with tosylchloride and methanesulfonyl chloride. Then, the desired molecules were synthesized by adding diethoxyphosphonate to the aldehyde group. Also, novel synthesis of hybrid compounds (<jats:bold>4a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> and <jats:bold>5a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold>) were tested toward some metabolic enzymes like carbonic anhydrase I and II isoenzymes (hCA I and hCA II) and acetylcholinesterase (AChE) enzyme. The synthesis of hybrid compounds (<jats:bold>4a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold> and <jats:bold>5a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold>) showed K<jats:sub>i<\/jats:sub> values of in range of 25.084\u00b14.73\u201069.853\u00b115.19\u2005nM against hCA I, 32.325\u00b11.67\u201382.761\u00b122.73\u2005nM against hCA II and 1.699\u00b10.25 and 3.500\u00b10.91\u2005nM against AChE. For these compounds, compound <jats:bold>4c<\/jats:bold> showed maximum inhibition effect against hCA I and hCA II isoenzymes and compound <jats:bold>5b<\/jats:bold> showed maximum inhibition effect against AChE enzyme. By performing docking studies of the most active compounds for their binding modes and interactions were determined.<\/jats:p>","DOI":"10.1002\/cbdv.202100787","type":"journal-article","created":{"date-parts":[[2022,3,22]],"date-time":"2022-03-22T15:03:46Z","timestamp":1647961426000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Enzyme Inhibition Properties and Molecular Docking Studies of 4\u2010Sulfonate Containing Aryl \u03b1\u2010Hydroxyphosphonates Based Hybrid Molecules"],"prefix":"10.1002","volume":"19","author":[{"given":"\u0130rfan","family":"\u015eahin","sequence":"first","affiliation":[{"name":"Department of Chemistry Faculty of Sciences and Arts Kahramanmaras Sutcu Imam University  TR 46100 Kahramanmaras Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zeynebe","family":"Bing\u00f6l","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Sciences Ataturk University  25240-Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sultan","family":"Onur","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Sciences and Arts Kahramanmaras Sutcu Imam University  TR 46100 Kahramanmaras Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Seyit Ali","family":"G\u00fcng\u00f6r","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Sciences and Arts Kahramanmaras Sutcu Imam University  TR 46100 Kahramanmaras Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Muhammet","family":"K\u00f6se","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Sciences and Arts Kahramanmaras Sutcu Imam University  TR 46100 Kahramanmaras Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u0130lhami","family":"G\u00fcl\u00e7in","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Sciences Ataturk University  25240-Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ferhan","family":"T\u00fcmer","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Sciences and Arts Kahramanmaras Sutcu Imam University  TR 46100 Kahramanmaras Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,4,5]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.45.12.3427-3432.2001"},{"key":"e_1_2_8_2_1","first-page":"2753","article-title":"\u2018Cell cycle arrest and apoptosis responses of human breast epithelial cells to the synthetic organosulfur compound p-methoxyphenyl p-toluenesulfonate\u2019","volume":"28","author":"Cyr L.","year":"2008","journal-title":"Anticancer Res."},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11356-012-1253-x"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.med.52.1.239"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.39.2.279"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-200363180-00001"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1093\/clinids\/8.1.163"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2015.1094658"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10532-014-9716-z"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/pi.1009"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/pola.1988.080260317"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biochi.2018.06.005"},{"key":"e_1_2_8_13_1","first-page":"144","article-title":"\u2018Synthesis, characterization, crystal structure and bioactivities of novel enamine and pyrrole derivatives endowed with acetylcholinesterase, a-glycosidase and human carbonic anhydrase inhibition effects\u2019","volume":"78","author":"Maharramov A.","year":"2021","journal-title":"Org. Commun."},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2021.105069"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2021.130492"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2016.1149479"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104554"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2020.114866"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2021.113486"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2017.11.079"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104171"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1198901"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103969"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.04.002"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103897"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1094470"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.12.012"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.sajb.2018.04.001"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.13149"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.02.013"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.11.001"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103762"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jff.2021.104602"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378867"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b05619"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1258319"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201100601"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.03.015"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.610080906"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00396-1"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo101743e"},{"key":"e_1_2_8_42_1","first-page":"3019","article-title":"\u2018The preparation of dialkyl 1-hydroxyalkylphosphonates in the reaction of trialkyl phosphites with oxonium salts derived from aldehydes or ketones\u2019","author":"Goldeman W.","year":"2006","journal-title":"Synthesis (Stuttg"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2017.05.029"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01318a036"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules190710103"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501573b"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201500035"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103312"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.03.077"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1403-5"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.01.019"},{"key":"e_1_2_8_52_1","first-page":"408","article-title":"\u2018Phenolic Compounds as Antioxidants: Carbonic Anhydrase Isoenzymes Inhibitors\u2019","volume":"13","author":"Gulcin I.","year":"2013","journal-title":"Mini Rev. Med. Chem."},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.04.007"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.12.054"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.2174\/138161206775193127"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms14035608"},{"key":"e_1_2_8_57_1","first-page":"54","article-title":"\u2018Butyrylcholinesterase: Structure and Physiological Importance\u2019","volume":"28","author":"\u00c7oku\u011fra\u015f A. N.","year":"2003","journal-title":"Turkish J. Biochem. -Turk J Biochem."},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701150"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2016.1170014"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1244533"},{"key":"e_1_2_8_62_1","first-page":"841","article-title":"\u2018The effects of melatonin hormone on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in\u2005vitro and in\u2005vivo\u2019","volume":"29","author":"Hisar O.","year":"2005","journal-title":"Turkish J. Vet. Anim. Sci."},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2014.999236"},{"key":"e_1_2_8_64_1","doi-asserted-by":"crossref","unstructured":"G.\u2005L. Ellman K.\u2005D. Courtney V. Andres J. F.\u2005R. M \u2018A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity\u2019 Biochem. Pharmacol.1961 7 88\u201395.","DOI":"10.1016\/0006-2952(61)90145-9"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2016.1156104"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21973"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1080\/13813455.2017.1360914"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21256"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B"},{"key":"e_1_2_8_70_1","unstructured":"D.\u2005S. Biovia \u2018Discovery studio visualizer\u2019 San Diego CA USA 2017 p. 298."},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10822-010-9395-8"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202100787","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.202100787","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202100787","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,21]],"date-time":"2023-08-21T21:03:31Z","timestamp":1692651811000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.202100787"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,5]]},"references-count":71,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2022,5]]}},"alternative-id":["10.1002\/cbdv.202100787"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.202100787","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,5]]},"assertion":[{"value":"2021-09-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-03-18","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-04-05","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202100787"}}