{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,7]],"date-time":"2026-04-07T22:06:19Z","timestamp":1775599579175,"version":"3.50.1"},"reference-count":37,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2013,1,24]],"date-time":"2013-01-24T00:00:00Z","timestamp":1358985600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A new series of amino\/nitro-substituted 3-arylcoumarins were synthesized and their antibacterial activity against clinical isolates of Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative) was evaluated. Some of these molecules exhibited antibacterial activity against S. aureus comparable to the standards used (oxolinic acid and ampicillin). The preliminary structure-activity relationship (SAR) study showed that the antibacterial activity against S. aureus depends on the position of the 3-arylcoumarin substitution pattern. With the aim of finding the structural features for the antibacterial activity and selectivity, in the present manuscript different positions of nitro, methyl, methoxy, amino and bromo substituents on the 3-arylcoumarin scaffold were reported.<\/jats:p>","DOI":"10.3390\/molecules18021394","type":"journal-article","created":{"date-parts":[[2013,1,24]],"date-time":"2013-01-24T11:29:13Z","timestamp":1359026953000},"page":"1394-1404","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":73,"title":["Synthesis and Structure-Activity Relationships of  Novel Amino\/Nitro Substituted 3-Arylcoumarins as  Antibacterial Agents"],"prefix":"10.3390","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3470-8299","authenticated-orcid":false,"given":"Maria","family":"Matos","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"given":"Saleta","family":"Vazquez-Rodriguez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"given":"Lourdes","family":"Santana","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"given":"Eugenio","family":"Uriarte","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"given":"Cristina","family":"Fuentes-Edfuf","sequence":"additional","affiliation":[{"name":"Departamento de Microbiolog\u00eda y Parasitolog\u00eda, Facultad de Biolog\u00eda, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"given":"Ysabel","family":"Santos","sequence":"additional","affiliation":[{"name":"Departamento de Microbiolog\u00eda y Parasitolog\u00eda, Facultad de Biolog\u00eda, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"given":"Angeles","family":"Mu\u00f1oz-Crego","sequence":"additional","affiliation":[{"name":"Departamento de Microbiolog\u00eda y Parasitolog\u00eda, Facultad de Biolog\u00eda, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2013,1,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"887","DOI":"10.2174\/0929867053507315","article-title":"Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity","volume":"12","author":"Borges","year":"2005","journal-title":"Curr. Med. Chem."},{"key":"ref_2","first-page":"23","article-title":"Simple coumarins: Privileged scaffolds in medicinal chemistry","volume":"4","author":"Borges","year":"2009","journal-title":"Front. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"752","DOI":"10.1021\/jm070909t","article-title":"Coumarin as Attractive Casein Kinase 2 (CK2) Inhibitor scaffold: An integrate approach to elucidate the putative binding motif and explain structure\u2013activity relationships","volume":"51","author":"Chilin","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"662","DOI":"10.1128\/AAC.22.4.662","article-title":"In vitro activity of DNA gyrase inhibitors, singly and in combination, against Mycobacterium avium complex","volume":"22","author":"Hooper","year":"1982","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3688","DOI":"10.1128\/AAC.00392-07","article-title":"Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening","volume":"51","author":"Ostrov","year":"2007","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4922","DOI":"10.1016\/j.bmcl.2010.06.048","article-title":"Synthesis, Selective anti-Helicobacter pylori activity, And cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides","volume":"20","author":"Chimenti","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_7","first-page":"1140","article-title":"Looking for new targets: Simple coumarins as antibacterial agents","volume":"8","author":"Matos","year":"2012","journal-title":"Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/j.bmcl.2005.10.013","article-title":"Design, Synthesis, and Vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids","volume":"16","author":"Vilar","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2665","DOI":"10.1016\/j.bmc.2007.11.038","article-title":"Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells","volume":"16","author":"Riveiro","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3543","DOI":"10.1016\/j.bmc.2010.03.069","article-title":"Design, Synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents","volume":"18","author":"Belluti","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3889","DOI":"10.1016\/j.bmcl.2010.05.022","article-title":"A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity","volume":"20","author":"Roussaki","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2514","DOI":"10.3390\/molecules14072514","article-title":"Tyrosinase inhibitor activity of coumarin-resveratrol hybrids","volume":"14","author":"Fais","year":"2009","journal-title":"Molecules"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3268","DOI":"10.1016\/j.bmcl.2009.04.085","article-title":"A New series of 3-phenylcoumarins as potent and selective MAO-B inhibitors","volume":"19","author":"Matos","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5157","DOI":"10.1016\/j.bmcl.2010.07.013","article-title":"New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors","volume":"20","author":"Matos","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"7127","DOI":"10.1021\/jm200716y","article-title":"Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors","volume":"54","author":"Matos","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5053","DOI":"10.1016\/j.bmcl.2009.07.039","article-title":"Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors","volume":"19","author":"Matos","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1016\/j.ejmech.2011.01.033","article-title":"Synthesis, Human monoamine oxidase inhibitory activity and molecular docking studies of 3-heteroarylcoumarin derivatives","volume":"49","author":"Delogu","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"383","DOI":"10.1126\/science.101.2624.383.a","article-title":"The antibacterial properties of dicumarol","volume":"101","author":"Goth","year":"1945","journal-title":"Science"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"10319","DOI":"10.1016\/j.bmc.2008.10.043","article-title":"Synthesis and antimicrobial activity of 2-alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones and 2-alkenylquinol-4-ones","volume":"16","author":"Hoettecke","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"956","DOI":"10.1016\/j.bmcl.2010.12.059","article-title":"Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents","volume":"21","author":"Shi","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"330","DOI":"10.1016\/j.molstruc.2010.11.016","article-title":"Synthesis, Characterization, In vitro antimicrobial and DNA cleavage studies of Co(II), Ni(II) and Cu(II) complexes with ONOO donor coumarin Schiff bases","volume":"985","author":"Patil","year":"2011","journal-title":"J. Mol. Struct."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1016\/j.ejmech.2010.12.015","article-title":"Synthesis of 4H-chromene, Coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities","volume":"46","author":"Sabry","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"ref_23","first-page":"67","article-title":"Antimicrobial activity of new coumarin derivatives","volume":"51","author":"Kawase","year":"2001","journal-title":"Arzneimittelforschung"},{"key":"ref_24","first-page":"84","article-title":"Synthesis, characterization and biological evaluation of some thiazolidinone derivatives as antimicrobial agents","volume":"2","author":"Patel","year":"2010","journal-title":"J. Chem. Pharm. Res."},{"key":"ref_25","first-page":"68","article-title":"Synthesis and characterization of some new thiazolidinones containing coumarin moiety and their antimicrobial study","volume":"2","author":"Patel","year":"2010","journal-title":"Arch. Appl. Sci. Res."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2079","DOI":"10.1016\/S0960-894X(99)00329-7","article-title":"Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase B","volume":"9","author":"Laurin","year":"1999","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1038\/431899a","article-title":"Antibiotics at the crossroads","volume":"431","author":"Nathan","year":"2004","journal-title":"Nature"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"775","DOI":"10.2174\/0929867043455774","article-title":"Challenges in antimicrobial drug discovery and the potential of nucleoside antibiotics","volume":"11","author":"Rachakonda","year":"2004","journal-title":"Curr. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Walsh, C. (2003). Antibiotics, Actions, Origins, Resistance, ASM.","DOI":"10.1128\/9781555817886"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5072","DOI":"10.1002\/anie.200600350","article-title":"Antibacterial natural products in medicinal chemistry - exodus or revival?","volume":"45","author":"Brands","year":"2006","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2763","DOI":"10.1055\/s-0029-1218835","article-title":"Regioselective synthesis of bromo-substituted 3-arylcoumarins","volume":"16","author":"Matos","year":"2010","journal-title":"Synthesis"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1225","DOI":"10.1016\/j.tetlet.2011.01.048","article-title":"Synthesis of 3-arylcoumarins via Suzuki-cross-coupling reactions of 3-chlorocoumarin","volume":"72","author":"Matos","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"ref_33","first-page":"49","article-title":"Nitro derivatives of 3-phenylcoumarins","volume":"7","author":"Krishnaswamy","year":"1969","journal-title":"Ind. J. Chem."},{"key":"ref_34","unstructured":"Rao, D.V., Sayigh, A.R., and Ulrich, H. (1972). Aminophenyl alkoxy coumarins. (3676436 A), US."},{"key":"ref_35","unstructured":"Kremky, E. (1979). Chromatographic method for the separation and identification of some coumarin derivatives. Organika, 159\u2013163."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"4250","DOI":"10.1021\/jm070100g","article-title":"Extensive SAR and computational studies of 3-{4-[(benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) Derivatives","volume":"50","author":"Piazzi","year":"2007","journal-title":"J. Med. Chem."},{"key":"ref_37","unstructured":"M cheminformatics, Bratislava, Slovak Republic. Available online:http:\/\/www.molinspiration.com\/services\/properties.html."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/2\/1394\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:44:30Z","timestamp":1760219070000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/2\/1394"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,1,24]]},"references-count":37,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2013,2]]}},"alternative-id":["molecules18021394"],"URL":"https:\/\/doi.org\/10.3390\/molecules18021394","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,1,24]]}}}