Synthesis, Characterization and Antimicrobial Activity of New Pyrrole Derivatives
Akbar Idhayadhulla, Radhakrishnan Surendra Kumar, and Abdul Jamal Abdul Nasser*
P.G. & Research Dept. of chemistry, Jamal Mohamed College, Tiruchirappalli– 620020, Tamil Nadu, India. jamal_abdulchem@gmail.com
Received April 12, 2011.
Accepted August 9, 2011.
Abstract
Here we describe pyrrole derivatives with potent antibacterial and antifungal activity. A new series of pyrrole 3a–e derivatives were synthesized using standard amination reactions. All the compounds presented here were obtained with high yields and under easy experimental conditions. Synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectra and mass spectral fragmentation. Synthesized compounds were screened against E. coli and S. aureus for antibacterial activity, as well as against A. niger and C. albicans for antifungal activity. We were able to obtain compounds with higher or equal potency to the reference compounds (Ciprofloxacin and Clotrimazole). Our data shows that a 4–hydroxyphenyl ring in our most potent compound seems to be responsible for antifungal activity against C. albicans. Incorporation of a 4–hydroxyphenyl ring as a pharmacophoric feature against C. albicans is a promising prospect.
Key words: Pyrrole derivative, antimicrobial activity, structure–activity relationship.
Resumen
Se describe la síntesis de una nueva serie de derivados pirrólicos con potente actividad antibacterial y antifúngica. La serie de compuestos 3a–e se sintetizó empleando reacciones de afinación estándar. Todos los compuestos preparados se obtuvieron en elevados rendimientos y bajo fáciles condiciones experimentales. Estos compuestos se caracterizaron por IR, RMN 1H, RMN 13C, y su estudio de fragmentación en espectrometría de masas. Los compuestos sintetizados se evaluaron en su actividad antibacterial contra E. coli y S. aureus, y en su actividad antifúngica contra A. niger y C. albicans. Se lograron obtener compuestos con una potencia mayor o igual a los compuestos de referencia: ciprofloxacina y clotrimazol. Los datos muestran que el anillo 4–hidroxifenilo en el compuesto más activo parece ser el grupo farmacóforo responsable de la actividad antifúngica contra C. albicans.
Palabras clave: Derivados pirrólicos, actividad antimicrobiana, relación estructura–actividad.
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