Synthesis of 6-sulfamoyl-4-oxoquinoline-3-carboxylic acid derivatives as integrase antagonists with anti-HIV activity

Design, Practical Synthesis, and Biological Evaluation of Novel 6-(Pyrazolylmethyl)-4-quinoline-3-carboxylic Acid Derivatives as HIV-1 Integrase Inhibitors

“…On the basis of the above information as well as on our interest in the development of new potential anti-HIV agents [ 12 ], we decided to explore the effect of chemical structure modification on the quinoline-3-carboxylic acid scaffold by decorating it at the N-1 and C-6 positions, with the aim of gaining further SAR data for anti-IN activity. We prepared the final compounds 11 –16 ( Figure 1 ) based on the following considerations: (1) A large number of compounds with important biological and pharmaceutical activities contain pyrazoles as a key substructure [ 13 , 14 ] and its planar structure may facilitate the π stacking interaction with target enzymes similar to a phenyl ring, so it is very interesting to design novel biologically active compounds by bringing the pyrazole moieties into the quinolone-3-carboxylic acid molecular framework with a view to study their additive effect on anti-IN properties.…”