{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T04:50:31Z","timestamp":1791867031389,"version":"4.3.4"},"reference-count":31,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2020,1,9]],"date-time":"2020-01-09T00:00:00Z","timestamp":1578528000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this paper, we aimed to exploit and combine in the same molecule the carbazole and the 1,3,4-oxadiazole pharmacophores, to obtain novel carprofen derivatives, by using two synthesis pathways. For the first route, the following steps have been followed: (i) (RS)-2-(6-chloro-9H-carbazol-2-yl)propanonic acid (carprofen) treatment with methanol, yielding methyl (RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate; (ii) the resulted methylic ester was converted to (RS)-2-(6-chloro-9H-carbazol-2-yl)propane hydrazide (carprofen hydrazide) by treatment with hydrazine hydrate; (iii) reaction of the hydrazide derivative with acyl chlorides led to N-[(2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoil]-N\u2032-R-substituted-benzoylhydrazine formation, which; (iv) in reaction with phosphorus oxychloride gave the (RS)-1-(6-chloro-9H-carbazol-2-yl)-1-(1,3,4-oxadiazol-2-yl)ethane derivatives. In the second synthesis pathway, new 1,3,4-oxadiazole ring compounds were obtained starting from carprofen which was reacted with isoniazid, in the presence of phosphorus oxychloride to form (RS)-1-(6-chloro-9H-carbazol-2-yl)-1-[5-(4-pyridyl)-1,3,4-oxadiazol-2-yl]ethane. The synthesized compounds were characterized by IR, 1H-NMR and 13C-NMR, screened for their drug-like properties and evaluated for in vitro cytotoxicity and antimicrobial activity. The obtained compounds exhibited a good antimicrobial activity, some of the compounds being particularly active on E. coli, while others on C. albicans. The most significant result is represented by their exceptional anti-biofilm activity, particularly against the P. aeruginosa biofilm. The cytotoxicity assay revealed that at concentrations lower than 100 \u03bcg\/mL, the tested compounds do not induce cytotoxicity and do not alter the mammalian cell cycle. The new synthesized compounds show good drug-like properties. The ADME-Tox profiles indicate a good oral absorption and average permeability through the blood brain barrier. However, further research is needed to reduce the predicted mutagenic potential and the hepatotoxicity.<\/jats:p>","DOI":"10.3390\/molecules25020266","type":"journal-article","created":{"date-parts":[[2020,1,10]],"date-time":"2020-01-10T04:06:51Z","timestamp":1578629211000},"page":"266","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Design, Synthesis and In Vitro Characterization of Novel Antimicrobial Agents Based on 6-Chloro-9H-carbazol Derivatives and 1,3,4-Oxadiazole Scaffolds"],"prefix":"10.3390","volume":"25","author":[{"given":"Alexandra T.","family":"Bordei Telehoiu","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, \u201cCarol Davila\u201d University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7685-3291","authenticated-orcid":false,"given":"Diana C.","family":"Nu\u021b\u0103","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, \u201cCarol Davila\u201d University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miron T.","family":"C\u0103proiu","sequence":"additional","affiliation":[{"name":"Center for Organic Chemistry \u201cC.D. Nenitzescu\u201d, Romanian Academy, 202B Spl. Independentei, 060023 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Florea","family":"Dumitrascu","sequence":"additional","affiliation":[{"name":"Center for Organic Chemistry \u201cC.D. Nenitzescu\u201d, Romanian Academy, 202B Spl. Independentei, 060023 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9144-5528","authenticated-orcid":false,"given":"Irina","family":"Zarafu","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2216-3842","authenticated-orcid":false,"given":"Petre","family":"Ioni\u021b\u0103","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carmellina D.","family":"B\u0103diceanu","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, \u201cCarol Davila\u201d University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Speran\u021ba","family":"Avram","sequence":"additional","affiliation":[{"name":"Department of Anatomy, Animal Physiology and Biophysics, Faculty of Biology, University of Bucharest, 1-3 Ale. Portocalelor, 060101 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mariana C.","family":"Chifiriuc","sequence":"additional","affiliation":[{"name":"Research Institute of the University of Bucharest (ICUB) and Microbiology Immunology Department, Faculty of Biology, University of Bucharest, 1-3 Ale. Portocalelor, 060101 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9031-338X","authenticated-orcid":false,"given":"Coralia","family":"Bleotu","sequence":"additional","affiliation":[{"name":"\u0218tefan S. Nicolau Institute of Virology, Romanian Academy, 285 Mihai Bravu Avenue, 030304 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6212-594X","authenticated-orcid":false,"given":"Carmen","family":"Limban","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, \u201cCarol Davila\u201d University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,1,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"781","DOI":"10.1016\/j.arabjc.2011.08.013","article-title":"Synthesis and antimicrobial activities of 9H-carbazole derivatives","volume":"9","author":"Salih","year":"2016","journal-title":"Arab. J. 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