1,5-Diphenylpyrrole Derivatives as Antimycobacterial Agents. Probing the Influence on Antimycobacterial Activity of Lipophilic Substituents at the Phenyl Rings

Journal of Medicinal Chemistry
2008.0

Abstract

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).

Knowledge Graph

Similar Paper

1,5-Diphenylpyrrole Derivatives as Antimycobacterial Agents. Probing the Influence on Antimycobacterial Activity of Lipophilic Substituents at the Phenyl Rings
Journal of Medicinal Chemistry 2008.0
Antimycobacterial Agents. Novel Diarylpyrrole Derivatives of BM212 Endowed with High Activity toward Mycobacterium tuberculosis and Low Cytotoxicity
Journal of Medicinal Chemistry 2006.0
1,5-Diaryl-2-ethyl pyrrole derivatives as antimycobacterial agents: Design, synthesis, and microbiological evaluation
European Journal of Medicinal Chemistry 2009.0
New pyrrole derivatives as antimycobacterial agents analogs of BM212
Bioorganic & Medicinal Chemistry Letters 1999.0
Identification of a novel pyrrole derivative endowed with antimycobacterial activity and protection index comparable to that of the current antitubercular drugs streptomycin and rifampin
Bioorganic & Medicinal Chemistry 2010.0
Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria
ACS Medicinal Chemistry Letters 2020.0
Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N′-((E)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria
Journal of Medicinal Chemistry 2016.0
Antimycobacterial activity of diphenylpyraline derivatives
European Journal of Medicinal Chemistry 2008.0
Tapping into the antitubercular potential of 2,5-dimethylpyrroles: A structure-activity relationship interrogation
European Journal of Medicinal Chemistry 2022.0
Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives
Bioorganic & Medicinal Chemistry 2008.0