title: Synthesis of antitumor-active betulinic acid-derived hydroxypropargylamines by copper-catalyzend mannich reactions.
abstract: Several novel betulin derivates were prepared using Mannich reactions as a key step. Starting from 3-ethynyl-3-hydroxy-lup-20(29)-ene derivatives, copper-catalyzed Mannich reactions yielded hydroxypropargyl ammonium hydrochlorides or their corresponding methiodides. All compounds were screened in a sulforhodamine B assay for their antitumor activity using a panel of 9 human cancer cell lines. Some of these compounds showed significant cytotoxicity; they act by triggering apoptotic cell death as shown by additional acridine orange/propidium iodide assays, Trypan blue tests, DNA laddering experiments, and investigations of the cell cycle.
authors: Bereich Organische Chemie, Martin-Luther-Universität Halle-Wittenberg, Saale, Germany. rene.csuk@chemie.uni-halle.de
authors: René
authors: R
authors: Csuk
authors: Christoph
authors: C
authors: Nitsche
authors: Ronny
authors: R
authors: Sczepek
authors: Stefan
authors: S
authors: Schwarz
authors: Bianka
authors: B
authors: Siewert
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D018929:Cell Culture Techniques; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003300:Copper / Q000737:chemistry*; D015195:Drug Design; D006801:Humans; D008352:Mannich Bases; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D053978:Pentacyclic Triterpenes; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014315:Triterpenes / Q000737:chemistry*; D000094062:Betulinic Acid
chemical_list: D000970:Antineoplastic Agents; D008352:Mannich Bases; D053978:Pentacyclic Triterpenes; D011437:Propylamines; D014315:Triterpenes; C009054:propargylamine; D003300:Copper; D010293:Pargyline; D000094062:Betulinic Acid