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The synthesized molecules comprise an anomeric (triazolyl)methyl phosphonate or phosphate motif and a dodecyl chain or a (triazolyl)ethyl purine system at the amide moiety. Their synthesis involved a 1,3\u2010dipolar cycloaddition between\n                    <jats:italic>N<\/jats:italic>\n                    \u2010propargyl or\n                    <jats:italic>N<\/jats:italic>\n                    \u2010dodecyl glucuronamidyl azides with propargyl alcohol or propargyl bromide and further\n                    <jats:italic>O<\/jats:italic>\n                    \u2010phosphorylation or Arbuzov reaction, respectively, to furnish glucuronamidyl (triazolyl)methyl phosphate\/phosphonate derivatives.\n                    <jats:italic>N<\/jats:italic>\n                    \u2010Propargyl glucuronamidyl derivatives were then engaged in cycloaddition with 9\u2010azidoethyl\u20106\u2010chloropurine to afford 6\u2010chloropurine isonucleotides. Isonucleoside (triazolyl)methyl phosphonate\/phosphates containing a 3\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010dodecyl moiety displayed significant antiproliferative activities in chronic myeloid leukemia (K562) and breast cancer (MCF\u20107) cells with GI\n                    <jats:sub>50<\/jats:sub>\n                    values ranging from 20.4 to 11.8\u2009\u03bcM and were shown to induce apoptosis. These isonucleotides also exhibited significant and selective antibacterial activities against\n                    <jats:italic>Streptococcus pneumoniae<\/jats:italic>\n                    D39, a clinical serotype 2 strain, with MIC values of 17.20 and 4.23\u2009\u03bcM, with no activity against the Gram\u2010negative bacteria\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    . The most active compound was the (triazolyl)methyl phosphate\u2010containing isonucleotide with GI\n                    <jats:sub>50<\/jats:sub>\n                    values of 12.8 and 11.8\u2009\u03bcM in K562 and MCF\u20107 cells, respectively, and a MIC value of 4.23\u2009\u03bcM in\n                    <jats:italic>S. pneumoniae<\/jats:italic>\n                    D39.\n                  <\/jats:p>","DOI":"10.1002\/cmdc.70328","type":"journal-article","created":{"date-parts":[[2026,6,19]],"date-time":"2026-06-19T03:41:36Z","timestamp":1781840496000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of Novel\n                    <scp>d<\/scp>\n                    \u2010Glucopyranuronamide\u2010Based Nucleos(t)ide Analogs Bearing (Triazolyl)methyl Phosph(on)ate Motifs With Anticancer and Antibacterial Potential"],"prefix":"10.1002","volume":"21","author":[{"given":"Domingos 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