{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T19:05:36Z","timestamp":1774292736822,"version":"3.50.1"},"reference-count":40,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2025,2,9]],"date-time":"2025-02-09T00:00:00Z","timestamp":1739059200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Deanship of Scientific Research, Vice Presidency for Graduate Studies and Scientific Research, King Faisal University, Saudi Arabia","award":["KFU250349"],"award-info":[{"award-number":["KFU250349"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The synthesis of 7-O-carboxymethyl-4\u2032-fluoroisoflavone 4 and 7-O-carboxymethyl-4\u2032-fluoro-2-trifluormethylisoflavone 7 involved the cyclization of 2,4-dihydroxy-4\u2032-fluorodeoxybenzoin 1, followed by 7-O-alkylation with methyl bromoacetate and subsequent acid-catalyzed hydrolysis. The structures of the novel compounds were validated using a range of techniques, including XRD crystallography (1H, 19F, 13C)-NMR, and IR. Only interhalogen contacts were detected in 5, while they were completely lacking in 2 and 4, owing to the presence of crystalline ethanol in the crystal structure. The %F\u2026F in 5 was 12.2% based on Hirshfeld calculations. The aromatic \u03c0-\u03c0 stacking interactions were important only in 2 and 4 but not observed in 5. Isoflavones 4, 5, and 7 displayed anticancer activity against MCF-7 cancer cells, with IC50 values of 13.66, 15.43, and 11.73 \u00b5M, respectively.<\/jats:p>","DOI":"10.3390\/molecules30040795","type":"journal-article","created":{"date-parts":[[2025,2,12]],"date-time":"2025-02-12T11:08:51Z","timestamp":1739358531000},"page":"795","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Efficient Consecutive Synthesis of Fluorinated Isoflavone Analogs, X-Ray Structures, Hirshfeld Analysis, and Anticancer Activity Assessment"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6715-5478","authenticated-orcid":false,"given":"Mohammed Salah","family":"Ayoup","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Malak","family":"Daqa","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus 00970, Palestine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6254-6381","authenticated-orcid":false,"given":"Yousef","family":"Salama","sequence":"additional","affiliation":[{"name":"An-Najah Center for Cancer and Stem Cell Research, Faculty of Medicine and Health Sciences, An-Najah National University, P.O. Box 7, Nablus 00970, Palestine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rand","family":"Hazzam","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus 00970, Palestine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1527-5560","authenticated-orcid":false,"given":"Mohammed B.","family":"Hawsawi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Umm Al-Qura University, Makkah 21955, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Saied M.","family":"Soliman","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7014-6190","authenticated-orcid":false,"given":"Nawaf","family":"Al-Maharik","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Science College, An-Najah National University, P.O. 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