The potential of click reactions for the synthesis of bioactive triterpenes

Bioorganic & Medicinal Chemistry Letters
René Csuk, Hans-Peter Deigner

Abstract

Click reactions between alkynes and azides using the privileged scaffold of triterpenes have been of interest for biological chemistry. Many publications deal with the synthesis of novel bioactive molecules; these conjugates have also been used for bioanalytical and diagnostic purposes. As a result, conjugates of better physicochemical properties were obtained; even compounds of improved solubility in water and physiological fluids were made through the introduction of a triazol residue. "Hybrid-structures", i.e. molecules consisting of two independently bioactive subunits linked by a triazole residue were higher bioactive than their parent compounds but not as active as expected, and with a few exceptions the ultimate breakthrough has not yet been achieved. Only in the synthesis of compounds with anti-leishmanial activity some new and promising lead structures were found. As a consequence, triazole modified triterpenes seem to hold their greatest future prospect rather as diagnostic reagents and molecular probes than as drugs.

Citations

Sep 10, 2019·European Journal of Medicinal Chemistry·Jiri HodonMilan Urban
Feb 12, 2021·International Journal of Molecular Sciences·Oxana KazakovaLucie Fischer
Sep 7, 2019·Journal of Natural Products·Oxana B KazakovaKyrill Yu Suponitsky

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