SYNTHESIS AND CHARACTERIZATION OF NEW IMINE AND PTHALIC ACID DERIVATIVES OF URSOLIC ACID
Keywords:Ursolic acid, Alkyl halide, Nucleophilic substitution, Anti-cancer
Objective: The current work envisages synthesis of novel ursolic acid derivatives and characterization by spectral methods that can be possible candidates for anti-inflammatory and anticancer activity.
Methods: A series of imine and phthalic acid derivatives of ursolic acid (3Î²-hydroxyurs-12-en-28-oic acid), have been synthesized. 3-hydroxyimino-urs-12-en-28-olic acid was treated with alkyl halide in the presence of sodium hydride in ethanol to yield 3-alkyloxyimino-urs-12-en-28-oic acid and further converted to its ester derivatives. Ursolic acid was reacted with phthalic anhydride in pyridine to get mono and di-substituted ester derivatives.
Results: Novel substituted imino and pthalic derivatives were synthesized. The compounds synthesized were characterized by MS, IR, 1H and C-NMR spectroscopy.
Conclusion: The derivatives prepared may facilitate designing of similar newer analogues which may be useful for generating possible candidates from ursolic acid for anti-imflammatory and anti-cancer potential. Ursolic acid oximes and its anhydrides exhibit valuable biological properties and are important starting materials for further transformations.
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