Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones.

Dai, Jiang-Kun; Dan, Wen-Jia; Li, Na; Du, Hong-Tao; Zhang, Ji-Wen; Wang, Jun-Ru

Dai, Jiang-Kun; Dan, Wen-Jia; Li, Na; Du, Hong-Tao; Zhang, Ji-Wen; Wang, Jun-Ru.

Afiliación

Dai JK; College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
Dan WJ; College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
Li N; College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
Du HT; College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
Zhang JW; College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
Wang JR; College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. Electronic address: wangjunru@nwsuaf.edu.cn.

Bioorg Med Chem Lett ; 26(2): 580-583, 2016 Jan 15.

Article en En | MEDLINE | ID: mdl-26681509

RESUMEN

An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (µg·mL(-)(1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (µg·mL(-)(1)) against Staphylococcus aureus.

Asunto(s)

Antibacterianos/química; Antibacterianos/farmacología; Carbolinas/química; Carbolinas/farmacología; Alcaloides Indólicos/química; Alcaloides Indólicos/farmacología; Staphylococcus aureus/efectos de los fármacos; Alquilación; Antibacterianos/síntesis química; Carbolinas/síntesis química; Humanos; Alcaloides Indólicos/síntesis química; Pruebas de Sensibilidad Microbiana; Infecciones Estafilocócicas/tratamiento farmacológico; Relación Estructura-Actividad

Palabras clave

3-N-alkylation; 3-N-benzylation; Antibacterial; Canthin-6-one; Staphylococcus aureus; Structureactivity relationship; Synthesis

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Staphylococcus aureus / Carbolinas / Alcaloides Indólicos / Antibacterianos Límite: Humans Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2016 Tipo del documento: Article País de afiliación: China Pais de publicación: Reino Unido

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