title: Synthesis and cytotoxic activity of pentacyclic triterpenoid sulfamates.
abstract: Methyl triterpenoates derived from oleanolic, ursolic, betulinic, glycyrrhetinic, platanic, or maslinic acid were converted into their corresponding sulfamates and carbamoylsulfamates. The sulfamates were screened in photometric sulforhodamine assays for cytotoxic activity employing several human tumor cell lines. Many of the compounds showed EC50 values in one-digit μM concentration. Of special interest seems methyl (3β) 3-(aminosulfonyloxy)-11-oxo-oleanoate (18) showing good cytotoxicity for the human adenocarcinomic alveolar basal epithelial cell line A549 while being less toxic for non-malignant NIH 3T3 mouse fibroblasts.
authors.affiliation: Martin-Luther-Universit, ä, t Halle-Wittenberg, Bereich Organische Chemie, Halle (Saale), Germany.
authors.forename: Sven
authors.initials: S
authors.lastname: Sommerwerk
authors.forename: Lucie
authors.initials: L
authors.lastname: Heller
authors.forename: René
authors.initials: R
authors.lastname: Csuk
mesh_terms: D000230:Adenocarcinoma / Q000473:pathology*; D000077192:Adenocarcinoma of Lung; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008175:Lung Neoplasms / Q000473:pathology*; D061986:MCF-7 Cells; D051379:Mice; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D053978:Pentacyclic Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D053978:Pentacyclic Triterpenes; D013451:Sulfonic Acids; C005741:sulfamic acid
keywords: Carbamoylsulfamates; Cytotoxic activity; Sulfamates; Triterpenoids