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To integrate the tetramethylpyrazine moiety into these novel molecules, the multifunctional natural chemical ligustrazine was employed.<\/jats:p><\/jats:sec><jats:sec><jats:title>Methods:<\/jats:title><jats:p>A variety of newly synthesized ligustrazine-based chalcones were utilized as precursors for the synthesis of new oximes and their inhibitory activity against COX-1, COX-2, and LOX-5 enzymes were compared.<\/jats:p><\/jats:sec><jats:sec><jats:title>Results:<\/jats:title><jats:p>The conversion of ketones to their oxime derivatives increased the effectiveness of COX-1 and COX-2 inhibition. Due to the substituted ether groups, oxime derivative 5d had the lowest IC50 values of 0.027 \u00b1 0.004 \u03bcM and 0.150 \u00b1 0.027 \u03bcM for COX-1 and COX-2 isoenzymes, respectively. Notably, the oxime derivative's highest effectiveness is conferred by the presence of methoxymethoxy or hydroxy groups at the C-3 and C-4 positions on the phenyl ring. The 6b derivative with a long alkyl chain ether group was shown to be the most powerful 5-LOX inhibitor. All compounds were also assessed for their ability to inhibit nitric oxide generation and LPS-induced IL-6, IL-1\u03b2, and TNF-\u03b1 production in RAW 264.7 macrophages. Finally, in order to determine the structural effects responsible for the binding mechanism of compounds, they were docked into the binding sites of COX-1, COX-2, and 5-LOX, which revealed an inhibitory mechanism of action and demonstrated the relevance of various types of interactions.<\/jats:p><\/jats:sec><jats:sec><jats:title>Conclusion:<\/jats:title><jats:p>The findings showed that these novel compounds had a significant impact on antiinflammatory actions.<\/jats:p><\/jats:sec>","DOI":"10.2174\/1573406419666230112110306","type":"journal-article","created":{"date-parts":[[2023,1,13]],"date-time":"2023-01-13T05:39:22Z","timestamp":1673588362000},"page":"669-685","update-policy":"https:\/\/doi.org\/10.2174\/bsp_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Discovery of Novel Tetramethylpyrazine Containing Chalcone Derivatives as Anti-Inflammatory Agents"],"prefix":"10.2174","volume":"19","author":[{"given":"Syed Nasir Abbas","family":"Bukhari","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Aljouf, Sakaka, 2014, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohamed Abdelwahab","family":"Abdelgawad","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Aljouf, Sakaka, 2014, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad Wahab","family":"Amjad","sequence":"additional","affiliation":[{"name":"Center for Ultrasound Molecular Imaging and Therapeutics, Pittsburgh Heart, Lung, Blood and Vascular Medicine Institute, University of Pittsburgh, Pittsburgh, PA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad Usman","family":"Munir","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Aljouf, Sakaka, 2014, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fatima Akbar","family":"Sheikh","sequence":"additional","affiliation":[{"name":"Al-Raziq College of Pharmacy, University of Sargodha, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"965","reference":[{"key":"ref=1","doi-asserted-by":"publisher","first-page":"200","DOI":"10.1038\/s41573-020-00114-z","volume":"20","author":"Atanasov A.G.","year":"2021","unstructured":"Atanasov A.G.; Zotchev S.B.; Dirsch V.M.; Supuran C.T.; Banach M.; Rollinger J.M.; Barreca D.; Weckwerth W.; Bauer R.; Bayer E.A.; Majeed M.; Bishayee A.; Bochkov V.; Bonn G.K.; Braidy N.; Bucar F.; Cifuentes A.; D\u2019Onofrio G.; Bodkin M.; Diederich M.; Dinkova-Kostova A.T.; Efferth T.; El Bairi K.; Arkells N.; Fan T-P.; Fiebich B.L.; Freissmuth M.; Georgiev M.I.; Gibbons S.; Godfrey K.M.; Gruber C.W.; Heer J.; Huber L.A.; Ibanez E.; Kijjoa A.; Kiss A.K.; Lu A.; Macias F.A.; Miller M.J.S.; Mocan A.; M&#xFC;ller R.; Nicoletti F.; Perry G.; Pittal&#xE0; V.; Rastrelli L.; Ristow M.; Russo G.L.; Silva A.S.; Schuster D.; Sheridan H.; Skalicka-Wo&#x17A;niak K.; Skaltsounis L.; Sobarzo-S&#xE1;nchez E.; Bredt D.S.; Stuppner H.; Sureda A.; Tzvetkov N.T.; Vacca R.A.; Aggarwal B.B.; Battino M.; Giampieri F.; Wink M.; Wolfender J-L.; Xiao J.; Yeung A.W.K.; Lizard G.; Popp M.A.; Heinrich M.; Berindan-Neagoe I.; Stadler M.; Daglia M.; Verpoorte R.; Supuran C.T.; Natural products in drug discovery: advances and opportunities. 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