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This structural feature is of high interest because it is present in many different bioactive molecules, many of which are well\u2010established pharmaceuticals. The introduction of a sulfone group into the N\u2010bridgehead system yields a new core structure containing a N\u2010bridgehead sulfonamide. While linear sulfonamides can be found in natural products, only artificial cyclic sulfonamides are known to date. Applications of related cyclic sulfonamide compounds include matrix metalloproteinase inhibitors, potential HIV and cancer therapeutics, and anti\u2010inflammatory compounds. To explore the potential bioactivity of the N\u2010bridgehead sulfonamide scaffold, a synthetic route toward these scaffolds is developed and their bioactivity is explored against different cancer cell lines.<\/jats:p>","DOI":"10.1002\/cmdc.202400936","type":"journal-article","created":{"date-parts":[[2025,5,14]],"date-time":"2025-05-14T03:29:46Z","timestamp":1747193386000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Designing Cyclic Nitrogen\u2010Bridged Sulfonamides with Anti\u2010Cancer Activity"],"prefix":"10.1002","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-5258-1609","authenticated-orcid":false,"given":"Benedikt W.","family":"Grau","sequence":"first","affiliation":[{"name":"Center for Experimental Therapeutics Oregon Health and Science University  Portland OR 97201 USA"},{"name":"Knight Cancer Institute Oregon Health and Science University  Portland OR 97201 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1034-5075","authenticated-orcid":false,"given":"Arpit","family":"Dheeraj","sequence":"additional","affiliation":[{"name":"Center for Experimental Therapeutics Oregon Health and Science University  Portland OR 97201 USA"},{"name":"Knight Cancer Institute Oregon Health and Science University  Portland OR 97201 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6254-3519","authenticated-orcid":false,"given":"Irimpan I.","family":"Mathews","sequence":"additional","affiliation":[{"name":"Structural Molecular Biology SLAC National Accelerator Laboratory Stanford Synchrotron Radiation Lightsource  Menlo Park CA 94025 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dhanir","family":"Tailor","sequence":"additional","affiliation":[{"name":"Center for Experimental Therapeutics Oregon Health and Science University  Portland OR 97201 USA"},{"name":"Knight Cancer Institute Oregon Health and Science University  Portland OR 97201 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4056-5033","authenticated-orcid":false,"given":"Sanjay V.","family":"Malhotra","sequence":"additional","affiliation":[{"name":"Center for Experimental Therapeutics Oregon Health and Science University  Portland OR 97201 USA"},{"name":"Knight Cancer Institute Oregon Health and Science University  Portland OR 97201 USA"},{"name":"Department of Cell Developmental and Cancer Biology Oregon Health and Science University  Portland OR 97201 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,5,14]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.4c01122"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.2174\/1385272825666210525154330"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4OB01589D"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24071340"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-2999(95)00551-X"},{"key":"e_1_2_6_5_3","doi-asserted-by":"publisher","DOI":"10.4103\/0250-474X.40329"},{"key":"e_1_2_6_5_4","doi-asserted-by":"publisher","DOI":"10.1056\/NEJM199103213241201"},{"key":"e_1_2_6_5_5","doi-asserted-by":"publisher","DOI":"10.3390\/ijms19061668"},{"key":"e_1_2_6_5_6","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100946"},{"key":"e_1_2_6_5_7","doi-asserted-by":"publisher","DOI":"10.1021\/ol401144m"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/9781782621836"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/314235a0"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo102558u"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10593-017-2080-2"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/iub.1334"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2017.1350983"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.19933260305"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.09.021"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol200478p"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol006589o"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444909047337"},{"key":"e_1_2_6_16_2","unstructured":"b)G. 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