Kantlam Chamakuri, Srinivasa Murthy Muppavarapu, N. Yellu
Aug 3, 2016
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Journal
Medicinal Chemistry Research
Abstract
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, 13C 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.