Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1398842 | European Journal of Medicinal Chemistry | 2014 | 8 Pages |
•Sulfamates of methyl triterpenoates were synthesized.•Several compounds were inhibitors for carbonic anhydrase II.•They act as competitive enzyme inhibitors even in a low μmol concentration.•Small changes in constitution cause tremendous effects in their activity.
Carbonic anhydrase II, belonging to one of the most important enzyme groups of the human body, is a well-studied isozyme from the family of the carbonic anhydrases. Since it is involved in several physiological processes, it has been a pharmaceutical target for many years. In this study we synthesized a number of sulfamates derived from pentacyclic methyl triterpenoates, and we demonstrate their potential as carbonic anhydrase II inhibitors using the well-established photometric 4-nitrophenyl acetate assay. Inhibition constants, as an indicator of their inhibition strength, were in the micromolar range; one compound (10, methyl (3β) 3-(aminosulfonyloxy)-oleanoate) showed a Ki value as low as 0.3 μM. This Ki value is comparable to that of acetazolamide which is a potent carbonic anhydrase inhibitor and a drug for the treatment of glaucoma.
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