{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T20:58:03Z","timestamp":1790542683652,"version":"4.1.0"},"reference-count":42,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T00:00:00Z","timestamp":1788998400000},"content-version":"vor","delay-in-days":9,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Motivated by the promising antimicrobial and ecotoxicological effects of 4\u2010alkylamino\u20107\u2010chloroquinoline and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010alkylphthalimide derivatives, these privileged nuclei were linked to investigate how lipophilicity influences antibacterial activity and ecotoxicity. For this purpose, seven 4\u2010alkylamino\u20107\u2010chloroquinolines (\n                    <jats:bold>2a\u2013g<\/jats:bold>\n                    ) were prepared, of which four were used as precursors (\n                    <jats:bold>2a\u2013d<\/jats:bold>\n                    ) and reacted with different anhydrides. Using a clean synthetic approach, 4\u2010alkylamino\u20107\u2010chloroquinoline\u2013succinimides (\n                    <jats:bold>3a\u2013d<\/jats:bold>\n                    ) and \u2013phthalimides (\n                    <jats:bold>5a\u2013d<\/jats:bold>\n                    ) were obtained in yields of 60%\u201399% after only filtration with distilled water. In vitro assays were performed to determine the minimum inhibitory\/bactericidal concentration (MIC\/MBC) against\n                    <jats:italic>Klebsiella pneumoniae<\/jats:italic>\n                    ,\n                    <jats:italic>Pseudomonas aeruginosa<\/jats:italic>\n                    ,\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    , and\n                    <jats:italic>Streptococcus mutans<\/jats:italic>\n                    . Lipophilicity (log\n                    <jats:italic>P<\/jats:italic>\n                    ) and toxicity were predicted using the pkCSM program. In vitro toxicity tests on\n                    <jats:italic>Artemia salina<\/jats:italic>\n                    larvae were used as an indicator of ecotoxicity. 4\u2010Alkylamino\u20107\u2010chloroquinolines (\n                    <jats:bold>2b<\/jats:bold>\n                    ,\n                    <jats:bold>2f<\/jats:bold>\n                    ,\n                    <jats:bold>2g<\/jats:bold>\n                    ) revealed a moderate MIC of 156.25 \u00b5g\u00b7mL\n                    <jats:sup>\u22121<\/jats:sup>\n                    against Gram\u2010(\u2013) and Gram\u2010(+) bacteria, whose predicted toxicity does not pose a potential risk to human health. Results indicate a correlation between increased lipophilicity and higher ecotoxicity, where less lipophilic compounds were less toxic to\n                    <jats:italic>A. salina<\/jats:italic>\n                    (LC\n                    <jats:sub>50<\/jats:sub>\n                    133.01\u2013777.50 \u00b5g\u00b7mL\n                    <jats:sup>\u22121<\/jats:sup>\n                    ) than 4\u2010alkylamino\u20107\u2010chloroquinoline\u2013phthalimides, suggesting further investigation of their cytotoxicity.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.71688","type":"journal-article","created":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T10:31:19Z","timestamp":1789036279000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Clean Synthesis of\n                    <i>N<\/i>\n                    \u20104\u2010Alkylamino\u20107\u2010chloroquinoline Cyclic Imides: Influence of Lipophilicity on Antibacterial and Ecotoxicological Properties"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-5750-1934","authenticated-orcid":false,"given":"Agenor P.","family":"Luz\u2010Filho","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa em Bioenergia e S\u00edntese Org\u00e2nica (LPBS) Department of Chemistry Universidade Federal da Para\u00edba (UFPB)  Jo\u00e3o Pessoa Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-5338-2201","authenticated-orcid":false,"given":"Thais C.","family":"Silva","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa em Bioenergia e S\u00edntese Org\u00e2nica (LPBS) Department of Chemistry Universidade Federal da Para\u00edba (UFPB)  Jo\u00e3o Pessoa Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-5451-2498","authenticated-orcid":false,"given":"Matheus B.","family":"Silva","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa em Bioenergia e S\u00edntese Org\u00e2nica (LPBS) Department of Chemistry Universidade Federal da Para\u00edba (UFPB)  Jo\u00e3o Pessoa Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-6585-2866","authenticated-orcid":false,"given":"Abra\u00e3o P.","family":"Sousa","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa em Bioenergia e S\u00edntese Org\u00e2nica (LPBS) Department of Chemistry Universidade Federal da Para\u00edba (UFPB)  Jo\u00e3o Pessoa Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1708-4066","authenticated-orcid":false,"given":"Helivaldo D. S.","family":"Souza","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa em Bioenergia e S\u00edntese Org\u00e2nica (LPBS) Department of Chemistry Universidade Federal da Para\u00edba (UFPB)  Jo\u00e3o Pessoa Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6731-4333","authenticated-orcid":false,"given":"Priscila S. 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