Bernthsen synthesis, antimicrobial activities and cytotoxicity of acridine derivatives

• Published in: Bioorganic & medicinal chemistry letters Vol. 20; no. 21; pp. 6324 - 6326
• Main Authors: Patel, Mehul M., Mali, Mimansha D., Patel, Saurabh K.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.11.2010; Elsevier
• Subjects: 4-(Acridin-9-ylmethyl)-2 H-(substituted chromen)-2-one; Acetic acid; acridine; Acridines - chemical synthesis; Acridines - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Anticancer activity; Antifungal activity; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Antimicrobial activity; Antimicrobial agents; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Antitumor activity; Aspergillus niger; Aspergillus niger - drug effects; Bacteria - drug effects; Biological and medical sciences; Condensation; Cytotoxicity; Escherichia coli; General aspects; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Indicators and Reagents; Magnetic Resonance Spectroscopy; Medical sciences; Microbial Sensitivity Tests; Pharmacology. Drug treatments; Pseudomonas aeruginosa; Spectrophotometry, Infrared; Staphylococcus aureus; Zinc chloride; Antifungal activity; Antibacterial activity; 4-(Acridin-9-ylmethyl)-2 H-(substituted chromen)-2-one; Anticancer activity; Pseudomonadales; Antineoplastic agent; Embryo; Nitrogen heterocycle; Acridine derivatives; Coumarine derivatives; Escherichia coli; Cytotoxicity; Oxygen heterocycle; Antimicrobial agent; Kidney; Fungi; 4-(Acridin-9-ylmethyl)-2H-(substituted chromen)-2-one; Antifungal agent; Structure activity relation; Chlorine Organic compounds; Bacteria; Micrococcales; Pseudomonadaceae; Pseudomonas aeruginosa; Micrococcaceae; Aromatic compound; Larynx; Fungi Imperfecti; Chemical synthesis; Tumor cell; Staphylococcus aureus; Enterobacteriaceae; Human; Promyelocytic leukemia; Lactone; Tricyclic compound; In vitro; HL60 cell line; Cell line; Aspergillus niger; Phenols; Antibacterial agent
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2010.06.001

The condensation reaction of diphenylamine with 2-oxo-2 H-(substituted chromen)-4-yl acetic acid in presence of anhydrous zinc chloride afford 4-(acridine-9-ylmethyl)-2 H-(substituted chromen)-2-one. The synthesized compounds were characterized by spectral studies and elemental analysis and screened for their in vitro antibacterial activity against Staphylococcus aureus, Staphylococcus pyogenes (gram +ve), Escherichia coli, Pseudomonas aeruginosa (gram −ve) and antifungal activity against Aspergillus niger and anticancer activity (HL-60, Hep-2 & HEK293T) by MTT assay. Chloro substituted compounds showed antimicrobial and anticancer activity with IC 50 values in the low micromolar range.