The potential of click reactions for the synthesis of bioactive triterpenes |
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Authors: | René Csuk Hans-Peter Deigner |
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Institution: | 1. Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany;2. Furtwangen University, Medical and Life Sciences Faculty, Jakob-Kienzle Str. 17, D-78054 Villingen-Schwenningen, Germany |
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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. |
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Keywords: | Click reactions Triterpene Azide-alkyne Cytotoxicity |
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