Abstract
3-Oxo-tirucall-8, 24-dien-3-one-21-oic acid is a minor natural product isolated from Boswellia serrata gum apart from β-boswellic acids. Since oxidation of 3-hydroxy group of β-boswellic acids leads to unstable beta-keto acids, Beckmann rearrangement could not be tried. Hence A-ring modified 3-oxo-tirucall-8, 24-dien-21 methyl esters (2–6) were synthesized for the first time via Beckmann rearrangement and evaluated for their anticancer potential against five human cancer cell lines (MCF-7, SW-982, HeLa, PC-3 and IMR-132) by MTT assay. While naturally occurring 3-oxo-tirucallic acid (1) and its methyl ester (2) exhibited nearly the same antiproliferative activity, A-ring modified molecules displayed improved anti-tumor activity with methyl A-homo-4-aza-3-oxo-tirucall-8, 24, dien-3-one-21-oate (4) exhibiting significant effect against prostate cancer cell lines.
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