{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T03:18:09Z","timestamp":1790565489922,"version":"4.1.0"},"reference-count":85,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2024,9,4]],"date-time":"2024-09-04T00:00:00Z","timestamp":1725408000000},"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":[[2024,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Acetaminophen, a centrally\u2010acting old analgesic drug, is a weak inhibitor of cyclooxygenase (COX) isoforms with some selectivity toward COX\u20102. This compound was used in this work as a precursor to create nine acetaminophen based coumarins (ACFs). To satisfy the aim of this work, which states the synthesis of acetaminophen\u2010based coumarins as selective COX\u20102 inhibitors, the ACFs were subjected to two types of investigation: <jats:italic>in\u2005vitro<\/jats:italic> and <jats:italic>in silico<\/jats:italic>. Given the former type, the ACFs capacity to block COX\u20101 and COX\u20102 was investigated in lab settings. On the other hand, the <jats:italic>in silico<\/jats:italic> investigation included docking the chemical structures of ACFs into the active sites of these enzymes, predicting their anticipated toxicities, and determining the ADME characteristics. The results of the <jats:italic>in\u2005vitro<\/jats:italic> study revealed that the synthesized ACFs demonstrated good\u2010to\u2010excellent inhibitory properties against the enzymes under study. Also, these ACFs exhibited a high level of COX\u20102 selectivity, which improved as the capacity of the aromatic substitute for withdrawing electrons was enhanced. Results of docking were comparable to the <jats:italic>in\u2005vitro<\/jats:italic> investigation in case of COX\u20102. On the other hand, the <jats:italic>in silico<\/jats:italic> investigations indicated that the synthesized ACFs are safer than their precursor, acetaminophen, with a high potential to consider oral\u2010administrated candidates.<\/jats:p>","DOI":"10.1002\/cbdv.202401309","type":"journal-article","created":{"date-parts":[[2024,7,16]],"date-time":"2024-07-16T09:46:14Z","timestamp":1721123174000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Synthesis of Acetaminophen\u2010Based Coumarins as Selective COX\u20102 Inhibitors: An <i>in\u2005vitro\u2010in silico<\/i> Study"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8198-8246","authenticated-orcid":false,"given":"Mahmood H. M.","family":"Jasim","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry College of Pharmacy University of Mosul  Mosul Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0926-7428","authenticated-orcid":false,"given":"Yasser Fakri","family":"Mustafa","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry College of Pharmacy University of Mosul  Mosul Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,9,4]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1080\/03007995.2022.2049551"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/prp2.835"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms23031566"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4RA00365A"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phrs.2016.02.020"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00204-024-03747-w"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.2147\/JPR.S143500"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2020.580289"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.eplepsyres.2018.06.016"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.2147\/JPR.S393809"},{"key":"e_1_2_7_11_1","first-page":"438","volume":"11","author":"Mustafa Y. F.","year":"2020","journal-title":"Syst. Rev. Pharm."},{"key":"e_1_2_7_12_1","first-page":"717","volume":"11","author":"Oglah M. K.","year":"2020","journal-title":"Syst. Rev. Pharm."},{"key":"e_1_2_7_13_1","first-page":"358","volume":"5","author":"Abdulaziz N. T.","year":"2023","journal-title":"Eurasian Chem. Commun."},{"key":"e_1_2_7_14_1","first-page":"981","volume":"76","author":"Jumintono J.","year":"2021","journal-title":"Arch. Razi Inst."},{"key":"e_1_2_7_15_1","first-page":"3711","volume":"64","author":"Mustafa Y. F.","year":"2021","journal-title":"Egypt. J. Chem."},{"key":"e_1_2_7_16_1","first-page":"1","volume":"15","author":"Mustafa Y. F.","year":"2021","journal-title":"Clin. Schizophr. Relat. Psychoses"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytol.2024.01.010"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12668-023-01100-6"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2024.137601"},{"key":"e_1_2_7_20_1","first-page":"1048","volume":"5","author":"Khalil R. R.","year":"2022","journal-title":"J. Med. Chem. Sci."},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2024.138193"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.clnesp.2022.04.019"},{"key":"e_1_2_7_23_1","doi-asserted-by":"crossref","unstructured":"H.\u2005A. Younes Y.\u2005F. Mustafa Indian J. Clin. Biochem.2023This is an article in press with the following DOI:https:\/\/doi.org\/10.1007\/s12291-023-01165-w","DOI":"10.1007\/s12291-023-01165-w"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcdf.2023.100395"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12291-023-01147-y"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.rechem.2023.100942"},{"key":"e_1_2_7_27_1","first-page":"598","volume":"11","author":"Mustafa Y. F.","year":"2020","journal-title":"Syst. Rev. Pharm."},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11418-019-01375-8"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-020-72840-8"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1186\/1758-2946-4-17"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.20035"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmgm.2005.12.005"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.07.054"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi1003298"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/prot.10465"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(95)80037-9"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1996.0897"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/prot.10232"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm050543p"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm061277y"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci800298z"},{"key":"e_1_2_7_42_1","first-page":"238","volume":"15","author":"Ranjbar M. M.","year":"2016","journal-title":"EXCLI J."},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gky318"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.3390\/jox13040039"},{"key":"e_1_2_7_45_1","first-page":"703","volume":"5","author":"Waheed S. A.","year":"2022","journal-title":"J. Med. Chem. Sci."},{"key":"e_1_2_7_46_1","first-page":"676","volume":"5","author":"Jasim S. F.","year":"2022","journal-title":"J. Med. Chem. Sci."},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2024.126027"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/prep.201300153"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11356-023-25913-w"},{"key":"e_1_2_7_50_1","first-page":"877","volume":"4","author":"Zain Al Abdeen S. H.","year":"2022","journal-title":"Eurasian Chem. Commun."},{"key":"e_1_2_7_51_1","first-page":"938","volume":"4","author":"Al Abdeen S. H. Z.","year":"2022","journal-title":"Eurasian Chem. Commun."},{"key":"e_1_2_7_52_1","first-page":"1171","volume":"4","author":"Al Abdeen S. H. Z.","year":"2022","journal-title":"Eurasian Chem. Commun."},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.2c00325"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12302-023-00779-4"},{"key":"e_1_2_7_55_1","first-page":"546","volume":"5","author":"Kasim S. M.","year":"2022","journal-title":"J. Med. Chem. Sci."},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11094-023-02874-5"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.2174\/0929867327999200917150939"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12032-023-02256-7"},{"key":"e_1_2_7_59_1","first-page":"579","volume":"30","author":"Jasim M. H. M.","year":"2021","journal-title":"Trop. J. Pharm. Res."},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1088\/1674-1056\/ac3655"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201700027"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0166-1280(98)00101-8"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-pharmtox-010919-023324"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1515\/chem-2023-0188"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep42717"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2020.109240"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.3390\/pharmaceutics15112523"},{"key":"e_1_2_7_68_1","first-page":"793","volume":"5","author":"Jasim S. F.","year":"2022","journal-title":"J. Med. Chem. Sci."},{"key":"e_1_2_7_69_1","first-page":"887","volume":"5","author":"Jasim S. F.","year":"2022","journal-title":"J. Med. Chem. Sci."},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11696-023-03105-7"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2023.137471"},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11696-024-03341-5"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phyplu.2023.100501"},{"key":"e_1_2_7_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2023.137415"},{"key":"e_1_2_7_75_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules29020287"},{"key":"e_1_2_7_76_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28248038"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13530-020-00056-4"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1475"},{"key":"e_1_2_7_79_1","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2018.00030"},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.5530\/pj.2023.15.23"},{"key":"e_1_2_7_81_1","first-page":"57","volume":"35","author":"Younis M. A.","year":"2023","journal-title":"Pharmakeftiki"},{"key":"e_1_2_7_82_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21020161"},{"key":"e_1_2_7_83_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2023.1122632"},{"key":"e_1_2_7_84_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00204-021-03142-9"},{"key":"e_1_2_7_85_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00204-021-03211-z"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202401309","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,8]],"date-time":"2025-01-08T17:47:12Z","timestamp":1736358432000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.202401309"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,9,4]]},"references-count":85,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2024,10]]}},"alternative-id":["10.1002\/cbdv.202401309"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.202401309","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,9,4]]},"assertion":[{"value":"2024-05-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-07-16","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-09-04","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202401309"}}