{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,25]],"date-time":"2026-07-25T00:00:11Z","timestamp":1784937611580,"version":"3.55.0"},"reference-count":50,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2024,9,12]],"date-time":"2024-09-12T00:00:00Z","timestamp":1726099200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"ARKAT Foundation, USA","award":["98760"],"award-info":[{"award-number":["98760"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Anthranilic acids, salicylaldehydes and arylboronic acids reacted in EtOH\/H2O (1\/3) at 150 \u00b0C under microwave irradiation for 1 h to give, in excellent yields and purity, twenty-three bridgehead bicyclo[4.4.0]boron heterocycles via one-pot, three-component green synthesis. The scope and the limitations of the reactions are discussed in terms of the substitution of ten different anthranilic acids, three salicylaldehydes and three arylboronic acids. The replacement of salicylaldehyde with o-hydroxyacetophenone demanded a lipophilic solvent for the reaction to occur. Eight novel derivatives were isolated following crystallization in a toluene-containing mixture that included molecular sieves. The above one-pot, three-component reactions were completed under microwave irradiation at 180 \u00b0C within 1.5 h, thus avoiding the conventional prolonged heating reaction times and the use of a Dean\u2013Stark apparatus. All derivatives were studied for their affinity to calf thymus DNA using proper techniques like viscosity and UV\u2013vis spectroscopy, where DNA-binding constants were found in the range 2.83 \u00d7 104\u20138.41 \u00d7 106 M\u22121. Ethidium bromide replacement studies using fluorescence spectroscopy indicated Stern\u2013Volmer constants between 1.49 \u00d7 104 and 5.36 \u00d7 104 M\u22121, whereas the corresponding quenching constants were calculated to be between 6.46 \u00d7 1011 and 2.33 \u00d7 1012 M\u22121 s\u22121. All the above initial experiments show that these compounds may have possible medical applications for DNA-related diseases.<\/jats:p>","DOI":"10.3390\/ijms25189842","type":"journal-article","created":{"date-parts":[[2024,9,12]],"date-time":"2024-09-12T02:30:23Z","timestamp":1726108223000},"page":"9842","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["One-Pot, Multi-Component Green Microwave-Assisted Synthesis of Bridgehead Bicyclo[4.4.0]boron Heterocycles and DNA Affinity Studies"],"prefix":"10.3390","volume":"25","author":[{"given":"Polinikis","family":"Paisidis","sequence":"first","affiliation":[{"name":"Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6378-1092","authenticated-orcid":false,"given":"Maroula G.","family":"Kokotou","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry, Department of Food Science and Human Nutrition, Agricultural University of Athens, Iera Odos 75, 11855 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antigoni","family":"Kotali","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry, Department of Chemical Engineering, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5879-7265","authenticated-orcid":false,"given":"George","family":"Psomas","sequence":"additional","affiliation":[{"name":"Laboratory of Inorganic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2186-2617","authenticated-orcid":false,"given":"Konstantina C.","family":"Fylaktakidou","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,9,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"512","DOI":"10.1016\/j.tetlet.2016.12.060","article-title":"New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid with \u03b2-keto butanoic acid N-acyl hydrazones","volume":"58","author":"Kotali","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"4117","DOI":"10.1055\/s-0035-1562610","article-title":"Synthesis of Bicyclic Boron Heterocycles Containing [1,3,4,2]Oxadiazaborole and [1,3,2]Oxazaborine","volume":"48","author":"Kotali","year":"2016","journal-title":"Synthesis"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"7245","DOI":"10.1016\/j.tet.2015.03.097","article-title":"Synthesis of novel dehydroacetic acid N-aroylhydrazone-derived boron heterocycles","volume":"71","author":"Kotali","year":"2015","journal-title":"Tetrahedron"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1631","DOI":"10.1002\/chem.201503943","article-title":"A Three-Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)","volume":"22","author":"Santos","year":"2015","journal-title":"Chem. 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