Synthesis and analgesic and anti-inflammatory activities of 7-azaindazole chalcone derivatives

摘要

A series of 7-azaindazole-chalcone (6a-j) derivatives were synthesized from 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde (4). The 5-bromo-1H-pyrazolo [3,4-b]pyridine (3) was subjected to Sommelet reaction to afford 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde (4), which underwent Claisen-Schmidt condensation with different substituted acetophenones (5a-j) in basic media to afford 7-azaindazole-chalcone (6a-j) derivatives. These compounds were characterized by their infrared, proton nuclear magnetic resonance, C-13 nuclear magnetic resonance, and mass spectral data. All these derivatives (6a-j) were evaluated for their anti-inflammatory and analgesic activities. Among the synthesized compounds 6j and 6i with CF3 group and 6d with Br group exhibited excellent anti-inflammatory activity, and the compound 6f with benzyloxyphenyl showed less anti-inflammatory activity when compared with the activity of standard reference, indomethacin. Further, these derivatives (6a-j) were evaluated for their analgesic activity. Among them, compounds 6e, 6d, 6j, and 6i exhibited excellent analgesic activity when compared with the activity of standard drug diclofenac sodium.