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In vitro antimicrobial evaluation of compounds\n                    <jats:bold>5a-d<\/jats:bold>\n                    and\n                    <jats:bold>7a-l<\/jats:bold>\n                    against different pathogenic bacterial and fungal strains revealed that compounds\n                    <jats:bold>5a<\/jats:bold>\n                    ,\n                    <jats:bold>5b<\/jats:bold>\n                    ,\n                    <jats:bold>5c<\/jats:bold>\n                    ,\n                    <jats:bold>7a<\/jats:bold>\n                    ,\n                    <jats:bold>7f<\/jats:bold>\n                    ,\n                    <jats:bold>7i<\/jats:bold>\n                    and\n                    <jats:bold>7k<\/jats:bold>\n                    displayed notable effectiveness against the Gram-positive bacteria,\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    and\n                    <jats:italic>Bacillus subtilis<\/jats:italic>\n                    , and the Gram-negative\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    , and all compounds lacked antifungal activity. In addition, compounds\n                    <jats:bold>5a<\/jats:bold>\n                    ,\n                    <jats:bold>5b<\/jats:bold>\n                    ,\n                    <jats:bold>5c<\/jats:bold>\n                    ,\n                    <jats:bold>7f<\/jats:bold>\n                    and\n                    <jats:bold>7\u00a0L<\/jats:bold>\n                    displayed marked anti-proliferative activity particularly against HepG-2 and MCF-7 cancer cell lines (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009&lt;\u200925 \u00b5M). The structures of compounds\n                    <jats:bold>5c<\/jats:bold>\n                    ,\n                    <jats:bold>7a<\/jats:bold>\n                    and\n                    <jats:bold>7f<\/jats:bold>\n                    were confirmed by single-crystal X-ray diffraction studies. Compound\n                    <jats:bold>5c<\/jats:bold>\n                    crystallized with a lattice water molecule and is stabilized by N\u2013H\u00b7\u00b7\u00b7Cl\/S, and C\u2013H\u00b7\u00b7\u00b7O\/Cl\/\u03c0 interactions. The crystal packing features of\n                    <jats:bold>7a<\/jats:bold>\n                    and\n                    <jats:bold>7f<\/jats:bold>\n                    are very similar, despite the presence of a methoxy substituent in\n                    <jats:bold>7f<\/jats:bold>\n                    . Compound\n                    <jats:bold>7a<\/jats:bold>\n                    is stabilized by C\u2013H\u00b7\u00b7\u00b7N\/S\/\u03c0 interactions and a chalcogen bond (S\u00b7\u00b7\u00b7\u03c0), whereas compound\n                    <jats:bold>7f<\/jats:bold>\n                    is stabilized by C\u2013H\u00b7\u00b7\u00b7N\/S\/\u03c0 interactions as well as C\u2013H\u00b7\u00b7\u00b7O interactions involving the methoxy oxygen as an acceptor. Molecular docking studies of the most potent antibacterial adamantane-thiazole derivatives\n                    <jats:bold>7f<\/jats:bold>\n                    and\n                    <jats:bold>7i<\/jats:bold>\n                    showed good affinity towards dehydrosqualene synthase (\n                    <jats:italic>Sa<\/jats:italic>\n                    CrtM) from\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    . Meanwhile, potent anti-proliferative compounds\n                    <jats:bold>5a<\/jats:bold>\n                    ,\n                    <jats:bold>5b<\/jats:bold>\n                    , and\n                    <jats:bold>7f<\/jats:bold>\n                    showed marked affinity the urokinase-type plasminogen activator receptor (uPAR).\n                  <\/jats:p>","DOI":"10.1186\/s13065-025-01706-9","type":"journal-article","created":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T09:07:02Z","timestamp":1768900022000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Adamantane-thiazole hybrids and related derivatives: synthesis, crystal structures, in vitro antibacterial, antifungal, and anti-proliferative activities"],"prefix":"10.1186","volume":"20","author":[{"given":"Heidi S. 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