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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

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Synthesis of certain pyrrole derivatives as antimicro-bial agents

Mosaad Mohamed1 / Ramdan El-Domany1 / Rania Abd El-Hameed1

Organic Chemistry Department Faculty of Pharmacy, Helwan University, Cairo, Egypt1

Microbiology and Immunology Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt2

This content is open access.

Citation Information: Acta Pharmaceutica. Volume 59, Issue 2, Pages 145–158, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: 10.2478/v10007-009-0016-9, June 2009

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Synthesis of certain pyrrole derivatives as antimicro-bial agents

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-carbonitriles (1b), 2-amino-3-carbamoyl-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrroles (2b), N-(3-cyano-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3b), N-(3-cyano-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3c), 2-amino-1-(4-methoxyphenyl)-4,5-diphenyl-3-tetrazolo-1H-pyrroles (5d), 7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-ones (7d), 7-(3-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione (9b) and N-(7-(2-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine)-N-aryl amines (10a)] showed potent antimicrobial activity.

Sinteza derivata pirola kao antimikrobnih tvari

U radu je opisana sinteza novih derivata pirola i pirolo[2,3-d]pirimidina s poboljšanim antimikrobnim djelovanjem. Reakcijom benzoina, primarnih aromatskih amina i malononitrila sintetizirana je serija novih 2-aminopirol-3-karbonitrila (1a-d), iz kojih su potom pripravljeni derivati pirola (2a-d do 5a-d) i pirolo[2,3-d]pirimidina (6a-d do 10a, d). Sintetiziranim spojevima ispitano je in vitro antimikrobno djelovanje na različite Gram-pozitivne, Gram-negativne bakterije i gljivice. Neki od sintetiziranih spojeva [2-amino-1-(2-metilfenil)-4,5-difenil-1H-pirol-3-karbonitril (1b), 2-amino-3-karbamoil-1-(3-metilfenil)-4,5-difenil-1H-pirol (2b), N-(3-cijano-1-(2-metilfenil)-4,5-difenil-1H-pirol-2-il)-acetamid (3b), N-(3-cijano-1-(3-metilfenil)-4,5-difenil-1H-pirol-2-il)-acetamid (3c), 2-amino-1-(4-metoksifenil)-4,5-difenil-3-tetrazolo-1H-pirol (5d), 7-(4-metoksifenil)-5,6-difenil-7H-pirolo[2,3-d]pirimidin-4(3H)-on (7d), 7(3-metilfenil)-5,6-difenil-7H-pirolo[2,3-d]pirimidin-4(3H)-tion (9b) i N-(7-(2-metilfenil)-5,6-difenil-7H-pirolo[2,3-d]pirimidin)-N-aril amin (10a)] imaju snažno antimikrobno djelovanje.

Keywords: pyrrole; pyrrolopyrimidine; antimicrobial activity

Keywords: pirol; pirolopirimidin; antimikrobno djelovanje

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