Abstract
A series of new natural product skeleton based 3-(halobenzyl)isocarbostyrils (2a–2i), were designed and synthesized to examine the effect of position of different halide substituents on anti-inflammatory activity. The structure–activity relationship shows a significant influence of position of halide substituents on in vitro anti-inflammatory activity. 3-(o-halobenzyl)isocarbostyrils (2a, 2d, and 2g) showed the lowest activity most probably due to the closure of pharmacophore site by intramolecular hydrogen bond between halides and N–H of amide. In contrast, 3-(p-halobenzyl)isocarbostyrils 2c, 2f, and 2i exhibited moderate to very good inflammatory activity. Compound 2c (IC50 = 251.002 ± 2.910) was found to have comparable activity with the standard drug (Indomethacin, IC50 = 271.210 ± 2.127). To further understand the effect of position of halide substituents on 3-(halobenzyl)isocarbostyrils, computational POM was carried out. The study with constructive propositions may be helpful for the design of more potent analogs.
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