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Title: A facile synthesis of N-phenyl-6-hydroxy-3-bromo-4-arylazo quinolin-2-ones under phase transfer catalytic conditions and studies on their antimicrobial activities
Authors: Sharma, Pratibha
Kumar, Ashok
Pandey, Priti
Keywords: Arylazo quinoline;phase transfer catalysis;antimicrobial activities
Issue Date: Sep-2006
Publisher: CSIR
IPC Code: Int.Cl.8 C07D
Abstract: The synthesis and characterization of N-phenyl-6-hydroxy-3-bromo-4-arylazoquinolin-2-ones has been reported under phase transfer catalytic conditions in 70% yields. Interaction of N-phenyl-2,5-dihydroxy-3-arylazo indoles with dibromocarbene under phase transfer catalysis conditions at 50-60oC and 600 r.p.m. results in a cycloaddition of the in situ generated carbene to the C=C bond followed by skeletal rearrangement in the indole frame work to yield quinoline nuclei. The structure of the compounds are established on the basis of their elemental, IR and 1H NMR and 13C NMR data. All the synthesized compounds have been evaluated for their in vitro growth inhibitory activity against Escherichia coli, Pseudomonas diminuta, Bascillus subtilis, Bacillus megaterium and Staphylococcus aureus. All the compounds show significant antibacterial activity. A perusal of data reveals that molecular refractive index (MR) is correlated linearly to the drug activity. The synthesized compounds have been subjected to acute toxicity studies to find out LD50 values. The compounds do not show any toxicity up to dose of 7.5 mg/kg body weights in rats.
Page(s): 2077-2082
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(09) [September 2006]

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