Synthesis, Electronic, and Antibacterial Properties of 3,7-Di(hetero)aryl-substituted Phenothiazinyl <i>N</i>-Propyl Trimethylammonium Salts.

Khelwati, Hilla; van Geelen, Lasse; Kalscheuer, Rainer; Müller, Thomas J J

Synthesis, Electronic, and Antibacterial Properties of 3,7-Di(hetero)aryl-substituted Phenothiazinyl N-Propyl Trimethylammonium Salts.

Khelwati, Hilla; van Geelen, Lasse; Kalscheuer, Rainer; Müller, Thomas J J.

Afiliación

Khelwati H; Institute of Organic Chemistry and Macromolecular Chemistry, Faculty of Mathematics and Natural Sciences, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
van Geelen L; Institute of Pharmaceutical Biology and Biotechnology, Faculty of Mathematics and Natural Sciences, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
Kalscheuer R; Institute of Pharmaceutical Biology and Biotechnology, Faculty of Mathematics and Natural Sciences, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
Müller TJJ; Institute of Organic Chemistry and Macromolecular Chemistry, Faculty of Mathematics and Natural Sciences, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.

Molecules ; 29(9)2024 May 03.

Article en En | MEDLINE | ID: mdl-38731617

ABSTRACT

ABSTRACT

In this study, a library of 3,7-di(hetero)aryl-substituted 10-(3-trimethylammoniumpropyl)10H-phenothiazine salts is prepared. These title compounds and their precursors are reversible redox systems with tunable potentials. The Hammett correlation gives a very good correlation of the first oxidation potentials with σp parameters. Furthermore, the title compounds and their precursors are blue to green-blue emissive. Screening of the salts reveals for some derivatives a distinct inhibition of several pathogenic bacterial strains (Mycobacterium tuberculosis, Staphylococcus aureus, Escherichia coli, Aconetobacter baumannii, and Klebsiella pneumoniae) in the lower micromolar range.

Asunto(s)

Antibacterianos; Pruebas de Sensibilidad Microbiana; Fenotiazinas; Antibacterianos/farmacología; Antibacterianos/síntesis química; Antibacterianos/química; Fenotiazinas/farmacología; Fenotiazinas/química; Fenotiazinas/síntesis química; Sales (Química)/química; Sales (Química)/farmacología; Staphylococcus aureus/efectos de los fármacos; Compuestos de Amonio Cuaternario/química; Compuestos de Amonio Cuaternario/farmacología; Compuestos de Amonio Cuaternario/síntesis química; Escherichia coli/efectos de los fármacos; Oxidación-Reducción; Bacterias/efectos de los fármacos; Estructura Molecular; Relación Estructura-Actividad

Palabras clave

Suzuki coupling; antibacterials; biological properties; cyclic voltammetry; fluorescence; heterocycles

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Fenotiazinas / Pruebas de Sensibilidad Microbiana / Antibacterianos Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Suiza

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