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Using cesium carbonate in the presence of 2-chloroacetamide and catalytic potassium iodide, \u03b1-mangostin (1) was subsequently transformed in three steps to provide ether 2, amide 3, and amine 4 in good yields at an optimum ratio of 1:3:3, respectively. The evaluation of the biological activities of \u03b1-mangostin and analogs 2\u20134 was described. Amine 4 showed promising cytotoxicity against the non-small-cell lung cancer H460 cell line fourfold more potent than that of cisplatin. Both compounds 3 and 4 possessed antitrypanosomal properties against Trypanosoma\u00a0brucei rhodesiense at a potency threefold stronger than that of \u03b1-mangostin. Furthermore, ether 2 gave potent SARS-CoV-2 main protease inhibition by suppressing 3-chymotrypsinlike protease (3CLpro) activity approximately threefold better than that of 1. Fragment molecular orbital method (FMO\u2013RIMP2\/PCM) indicated the improved binding interaction of 2 in the 3CLpro active site regarding an additional ether moiety. Thus, the series of N-containing \u03b1-mangostin analogs prospectively enhance druglike properties based on isosteric replacement and would be further studied as potential biotically active chemical entries, particularly for anti-lung-cancer, antitrypanosomal, and anti-SARS-CoV-2 main protease applications.<\/jats:p>","DOI":"10.3390\/molecules28031104","type":"journal-article","created":{"date-parts":[[2023,1,23]],"date-time":"2023-01-23T01:36:26Z","timestamp":1674437786000},"page":"1104","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["N-Containing \u03b1-Mangostin Analogs via Smiles Rearrangement as the Promising Cytotoxic, Antitrypanosomal, and SARS-CoV-2 Main Protease Inhibitory Agents"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0148-8039","authenticated-orcid":false,"given":"Nan Yadanar Lin","family":"Pyae","sequence":"first","affiliation":[{"name":"Pharmaceutical 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