Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis and Characterization of New Derivatives of (EZ)-N’-Benzylidene-(2RS)-2-(6-Chloro-9H-Carbazol-2-Yl)propanohydrazide as Potential Tuberculostatic Agents

Ilinca Margareta Vlad
,
Diana Camelia Nuță
* ORCID logo ,
Miron Theodor Căproiu
,
Florea Dumitrașcu
,
Eleonóra Kapronczai
ORCID logo ,
Georgiana Ramona Mük
ORCID logo ,
Speranta Avram
,
Adelina Gabriela Niculescu
,
Irina Zarafu
ORCID logo ,
Vanesa Alexandra Ciorobescu
,
Ana Maria Brezeanu
,
Carmen Limban
Version 1 : Received: 18 January 2024 / Approved: 19 January 2024 / Online: 19 January 2024 (07:00:53 CET)

A peer-reviewed article of this Preprint also exists.

Vlad, I.M.; Nuță, D.C.; Căproiu, M.T.; Dumitrașcu, F.; Kapronczai, E.; Mük, G.R.; Avram, S.; Niculescu, A.G.; Zarafu, I.; Ciorobescu, V.A.; Brezeanu, A.M.; Limban, C. Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents. Antibiotics 2024, 13, 212. Vlad, I.M.; Nuță, D.C.; Căproiu, M.T.; Dumitrașcu, F.; Kapronczai, E.; Mük, G.R.; Avram, S.; Niculescu, A.G.; Zarafu, I.; Ciorobescu, V.A.; Brezeanu, A.M.; Limban, C. Synthesis and Characterization of New N-acyl Hydrazone Derivatives of Carprofen as Potential Tuberculostatic Agents. Antibiotics 2024, 13, 212.

Abstract

N-acyl hydrazone (NAH) has been remarked as a promising scaffold in drug design, given its versatility, ease of synthesis, and appealing biological activities (i.e., 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. Thus, this study presents 6 new derivatives of (EZ)-N'-benzylidene-(2RS)-2-(6-chloro-9H-carbazol-2-yl)propanohydrazide that were obtained through a microwave-assisted synthesis method. In more detail, we have 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. Moreover, the compounds have been evaluated for their tuberculostatic activity, testing their effects on four M. tuberculosis strains (two of them 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 M. tuberculosis strains.

Keywords

N-acyl hydrazone derivatives; microwave synthesis; FT-IR spectral data; NMR analysis; HRMS analysis; tuberculostatic activity.

Subject

Chemistry and Materials Science, Medicinal Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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