1,5-Diphenylpyrrole derivatives as antimycobacterial agents. Probing the influence on antimycobacterial activity of lipophilic substituents at the phenyl rings.

Mariangela Biava, Giulio Cesare Porretta, Giovanna Poce, Alessandro De Logu, Manuela Saddi, Rita Meleddu, Fabrizio Manetti, Edda De Rossi, Maurizio Botta

Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università La Sapienza, Piazzale A. Moro 5, I-00185 Rome, Italy. mariangela.biava@uniroma.it

Journal of medicinal chemistry 2008 Jun 26

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Synthesis and biological evaluation of new derivatives of 1,5-bis(4-chlorophenyl)-2-methyl-3-(4-methylpiperazin-1-yl)methyl-1H-pyrrole (BM 212, 16) are reported. Variously substituted phenyl rings with different substitution pattern and lipophilicity were added to the pyrrole nucleus to evaluate their influence on the activity toward Mycobacterium tuberculosis (MTB) and atypical mycobacteria. The most active derivatives showed activity between 0.125-0.5 microg/mL (better than 16 and streptomycin) and protection index (64-256) higher than 16 (4) and similar to isoniazid and streptomycin (128).

Citation

Mariangela Biava, Giulio Cesare Porretta, Giovanna Poce, Alessandro De Logu, Manuela Saddi, Rita Meleddu, Fabrizio Manetti, Edda De Rossi, Maurizio Botta. 1,5-Diphenylpyrrole derivatives as antimycobacterial agents. Probing the influence on antimycobacterial activity of lipophilic substituents at the phenyl rings. Journal of medicinal chemistry. 2008 Jun 26;51(12):3644-8