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Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate

Four novel methyl 4-phenylpicolinoimidate derivatives of hydrazone have been synthesized and evaluated for their antimicrobial activity, including tuberculostatic activity. The compounds obtained are condensates of hydrazonamide or hydrazide with 5-nitro-2-furaldehyde or 5-nitro-2-thiophenecarboxald...

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Autores principales: Gobis, Katarzyna, Szczesio, Małgorzata, Olczak, Andrzej, Korona-Głowniak, Izabela, Augustynowicz-Kopeć, Ewa, Mazernt-Politowicz, Ida, Ziembicka, Dagmara, Główka, Marek L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9103619/
https://www.ncbi.nlm.nih.gov/pubmed/35591419
http://dx.doi.org/10.3390/ma15093085
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author Gobis, Katarzyna
Szczesio, Małgorzata
Olczak, Andrzej
Korona-Głowniak, Izabela
Augustynowicz-Kopeć, Ewa
Mazernt-Politowicz, Ida
Ziembicka, Dagmara
Główka, Marek L.
author_facet Gobis, Katarzyna
Szczesio, Małgorzata
Olczak, Andrzej
Korona-Głowniak, Izabela
Augustynowicz-Kopeć, Ewa
Mazernt-Politowicz, Ida
Ziembicka, Dagmara
Główka, Marek L.
author_sort Gobis, Katarzyna
collection PubMed
description Four novel methyl 4-phenylpicolinoimidate derivatives of hydrazone have been synthesized and evaluated for their antimicrobial activity, including tuberculostatic activity. The compounds obtained are condensates of hydrazonamide or hydrazide with 5-nitro-2-furaldehyde or 5-nitro-2-thiophenecarboxaldehyde. The antimicrobial activity of the tested compounds varied. Compound 3b exhibited significant activity against the tested Gram-positive bacteria (7.8–250 µg/mL). The results of structural tests revealed that the compound is the only one obtained in the form of a Z isomer. Tuberculostatic activity tests showed higher activity of derivatives 3a and 4a containing nitrofuran systems (MICs 3.1–12.5 µg/mL). This research allowed us to identify hydrazone 3b as a starting point for further optimization in the search for antimicrobial drugs. Likewise, compound 4a appears to be a good guiding structure for use in future research on new anti-tuberculosis drugs.
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spelling pubmed-91036192022-05-14 Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate Gobis, Katarzyna Szczesio, Małgorzata Olczak, Andrzej Korona-Głowniak, Izabela Augustynowicz-Kopeć, Ewa Mazernt-Politowicz, Ida Ziembicka, Dagmara Główka, Marek L. Materials (Basel) Article Four novel methyl 4-phenylpicolinoimidate derivatives of hydrazone have been synthesized and evaluated for their antimicrobial activity, including tuberculostatic activity. The compounds obtained are condensates of hydrazonamide or hydrazide with 5-nitro-2-furaldehyde or 5-nitro-2-thiophenecarboxaldehyde. The antimicrobial activity of the tested compounds varied. Compound 3b exhibited significant activity against the tested Gram-positive bacteria (7.8–250 µg/mL). The results of structural tests revealed that the compound is the only one obtained in the form of a Z isomer. Tuberculostatic activity tests showed higher activity of derivatives 3a and 4a containing nitrofuran systems (MICs 3.1–12.5 µg/mL). This research allowed us to identify hydrazone 3b as a starting point for further optimization in the search for antimicrobial drugs. Likewise, compound 4a appears to be a good guiding structure for use in future research on new anti-tuberculosis drugs. MDPI 2022-04-24 /pmc/articles/PMC9103619/ /pubmed/35591419 http://dx.doi.org/10.3390/ma15093085 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Gobis, Katarzyna
Szczesio, Małgorzata
Olczak, Andrzej
Korona-Głowniak, Izabela
Augustynowicz-Kopeć, Ewa
Mazernt-Politowicz, Ida
Ziembicka, Dagmara
Główka, Marek L.
Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate
title Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate
title_full Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate
title_fullStr Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate
title_full_unstemmed Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate
title_short Differences in the Structure and Antimicrobial Activity of Hydrazones Derived from Methyl 4-Phenylpicolinimidate
title_sort differences in the structure and antimicrobial activity of hydrazones derived from methyl 4-phenylpicolinimidate
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9103619/
https://www.ncbi.nlm.nih.gov/pubmed/35591419
http://dx.doi.org/10.3390/ma15093085
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