Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives.

Sivakumar, P.M.; Prabu Seenivasan, S.; Kumar, V.; Doble, M.

Bioorganic & Medicinal Chemistry Letters; 2007; 17; 1695–1700.

Abstract: In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure–activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C₂₄ was found to be the most active (~99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 m g/ml levels, followed by compound C ₂₁ . Four compounds at the 50 m g/ml and eight compounds at the 100 m g/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 m g/ml data. The statistical measures such as r , r 2 , q 2 , and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory ( q ² = 0.56) and it can be used for designing similar group of compounds.

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