Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents
N-acyl hydrazone (NAH) is recognized as a promising framework in drug design due to its versatility, straightforward synthesis, and attractive range of biological activities, including antimicrobial, antitumoral, analgesic, and anti-inflammatory properties. In the global context of increasing resist...
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| Format: | Article |
| Language: | English |
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MDPI AG
2024-02-01
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| Series: | Antibiotics |
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| Online Access: | https://www.mdpi.com/2079-6382/13/3/212 |
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| author | Ilinca Margareta Vlad Diana Camelia Nuță Miron Theodor Căproiu Florea Dumitrașcu Eleonóra Kapronczai Georgiana Ramona Mük Speranta Avram Adelina Gabriela Niculescu Irina Zarafu Vanesa Alexandra Ciorobescu Ana Maria Brezeanu Carmen Limban |
| author_facet | Ilinca Margareta Vlad Diana Camelia Nuță Miron Theodor Căproiu Florea Dumitrașcu Eleonóra Kapronczai Georgiana Ramona Mük Speranta Avram Adelina Gabriela Niculescu Irina Zarafu Vanesa Alexandra Ciorobescu Ana Maria Brezeanu Carmen Limban |
| author_sort | Ilinca Margareta Vlad |
| collection | DOAJ |
| description | N-acyl hydrazone (NAH) is recognized as a promising framework in drug design due to its versatility, straightforward synthesis, and attractive range of biological activities, including antimicrobial, antitumoral, analgesic, and anti-inflammatory properties. In the global context of increasing resistance of pathogenic bacteria to antibiotics, NAHs represent potential solutions for developing improved treatment alternatives. Therefore, this research introduces six novel derivatives of (<i>EZ</i>)-N’-benzylidene-2-(6-chloro-9<i>H</i>-carbazol-2-yl)propanehydrazide, synthesized using a microwave-assisted method. In more detail, we joined two pharmacophore fragments in a single molecule, represented by an NSAID-type carprofen structure and a hydrazone-type structure, obtaining a new series of NSAID-N-acyl hydrazone derivatives that were further characterized spectrally using FT-IR, NMR, and HRMS investigations. Additionally, the substances were assessed for their tuberculostatic activity by examining their impact on four strains of <i>M. tuberculosis</i>, including two susceptible to rifampicin (RIF) and isoniazid (INH), one susceptible to RIF and resistant to INH, and one resistant to both RIF and INH. The results of our research highlight the potential of the prepared compounds in fighting against antibiotic-resistant <i>M. tuberculosis</i> strains. |
| first_indexed | 2024-04-24T18:36:37Z |
| format | Article |
| id | doaj.art-5a5480f5373e44d68bd0e545ee717d3f |
| institution | Directory Open Access Journal |
| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-04-24T18:36:37Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antibiotics |
| spelling | doaj.art-5a5480f5373e44d68bd0e545ee717d3f2024-03-27T13:18:05ZengMDPI AGAntibiotics2079-63822024-02-0113321210.3390/antibiotics13030212Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic AgentsIlinca Margareta Vlad0Diana Camelia Nuță1Miron Theodor Căproiu2Florea Dumitrașcu3Eleonóra Kapronczai4Georgiana Ramona Mük5Speranta Avram6Adelina Gabriela Niculescu7Irina Zarafu8Vanesa Alexandra Ciorobescu9Ana Maria Brezeanu10Carmen Limban11Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no. 6, 020956 Bucharest, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no. 6, 020956 Bucharest, Romania“C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independenței, 060023 Bucharest, Romania“C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independenței, 060023 Bucharest, RomaniaDepartment of Chemistry, Supramolecular Organic and Organometallic Chemistry Centre, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany János, 400028 Cluj-Napoca, RomaniaFaculty of Biology, University of Bucharest, Splaiul Independenței 91-95, 050095 Bucharest, RomaniaFaculty of Biology, University of Bucharest, Splaiul Independenței 91-95, 050095 Bucharest, RomaniaResearch Institute of the University of Bucharest, Sos. Panduri 90-92, 050095 Bucharest, RomaniaDepartment of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no. 6, 020956 Bucharest, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no. 6, 020956 Bucharest, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no. 6, 020956 Bucharest, RomaniaN-acyl hydrazone (NAH) is recognized as a promising framework in drug design due to its versatility, straightforward synthesis, and attractive range of biological activities, including antimicrobial, antitumoral, analgesic, and anti-inflammatory properties. In the global context of increasing resistance of pathogenic bacteria to antibiotics, NAHs represent potential solutions for developing improved treatment alternatives. Therefore, this research introduces six novel derivatives of (<i>EZ</i>)-N’-benzylidene-2-(6-chloro-9<i>H</i>-carbazol-2-yl)propanehydrazide, synthesized using a microwave-assisted method. In more detail, we joined two pharmacophore fragments in a single molecule, represented by an NSAID-type carprofen structure and a hydrazone-type structure, obtaining a new series of NSAID-N-acyl hydrazone derivatives that were further characterized spectrally using FT-IR, NMR, and HRMS investigations. Additionally, the substances were assessed for their tuberculostatic activity by examining their impact on four strains of <i>M. tuberculosis</i>, including two susceptible to rifampicin (RIF) and isoniazid (INH), one susceptible to RIF and resistant to INH, and one resistant to both RIF and INH. The results of our research highlight the potential of the prepared compounds in fighting against antibiotic-resistant <i>M. tuberculosis</i> strains.https://www.mdpi.com/2079-6382/13/3/212N-acyl hydrazone derivativesmicrowave synthesisFT-IR spectral dataNMR analysisHRMS analysistuberculostatic activity |
| spellingShingle | Ilinca Margareta Vlad Diana Camelia Nuță Miron Theodor Căproiu Florea Dumitrașcu Eleonóra Kapronczai Georgiana Ramona Mük Speranta Avram Adelina Gabriela Niculescu Irina Zarafu Vanesa Alexandra Ciorobescu Ana Maria Brezeanu Carmen Limban Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents Antibiotics N-acyl hydrazone derivatives microwave synthesis FT-IR spectral data NMR analysis HRMS analysis tuberculostatic activity |
| title | Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents |
| title_full | Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents |
| title_fullStr | Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents |
| title_full_unstemmed | Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents |
| title_short | Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents |
| title_sort | synthesis and characterization of new n acyl hydrazone derivatives of carprofen as potential tuberculostatic agents |
| topic | N-acyl hydrazone derivatives microwave synthesis FT-IR spectral data NMR analysis HRMS analysis tuberculostatic activity |
| url | https://www.mdpi.com/2079-6382/13/3/212 |
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