Acta Pharm. 59 (2009) 145-158

full paper

Original research paper

Synthesis of certain pyrrole derivatives as antimicrobial agents

MOSAAD SAYED MOHAMED, RAMDAN AHMED EL-DOMANY and RANIA HELMY ABD EL-HAMEED

zeiadomar@yahoo.com

¹ Organic Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt

² Microbiology and Immunology Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt

Accepted April 3, 2009

In an effort to establish new pyrroles and pyrrolo[2,3-d]pyrimidines with improved antimicrobial activity we report here the synthesis and in vitro microbiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-d to 5a-d) and pyrrolo[2,3-d]pyrimidines (6a-d to 10a,d) were synthesized. The in vitro antimicrobial testing of the synthesized compounds was carried out against Gram-positive, Gram-negative bacteria and fungi. Some of the prepared compounds, [2-amino-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrole-3-carbonitrile (1b), 2-amino-3-carbamoyl-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrrole (2b), N-(3-cyano-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamide (3b), N-(3-cyano-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamide (3c), 2-amino-1-(4-methoxyphenyl)-4,5-diphenyl-3-tetrazolo-1H-pyrrole (5d), 7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (7d), 7(3-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thion (9b) and N-(7-(2-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine)-N-aryl amine (10a)] showed potent antimicrobial activity.

Keywords: pyrrole, pyrrolopyrimidine, antimicrobial activity