Synthesis and cytotoxicity of triterpenoid seven members cyclic amines

• Published in: Bioorganicheskaia khimiia Vol. 40; no. 2; p. 217
• Main Authors: Kazakova, O B, Giniiatullina, G V, Medvedeva, N I, Lopatina, T V, Baĭkova, I P, Tolstikov, G A, Apryshko, G N
• Format: Journal Article
• Language: Russian
• Published: Russia (Federation) 01-03-2014
• Subjects: Adamantane - chemical synthesis; Adamantane - chemistry; Antineoplastic Agents - administration & dosage; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antiviral Agents - administration & dosage; Antiviral Agents - chemistry; Cell Line, Tumor; Cell Proliferation - drug effects; Drug Screening Assays, Antitumor; Humans; Neoplasms - drug therapy; Neoplasms - pathology; Oleanolic Acid - analogs & derivatives; Oleanolic Acid - chemical synthesis; Oleanolic Acid - chemistry; Structure-Activity Relationship; Triterpenes - chemical synthesis; Triterpenes - chemistry
• ISSN: 0132-3423

Synthesis of 3-deoxy-3a-homo-3a-aza-derivatives of betulin and erythrodiol from betulonic and oleanonic acids was carried out. The most antineoplastic activity with a wide range of action at in vitro testing showed 3-deoxy-3a-homo-3a-aza-28-hydroxy-12(13)-oleanene, which by results of profound studying could be recommended for in vivo investigation. Its modification in the C28 position by introduction of amethoxycinnamoyl fragment led to a loss of antineoplastic activity. 3-Deoxy-3a-homo-3a-aza-derivatives of betulin (3-(aminopropyl)-, 28-(2-carboxyethyl)carboxy-, and 28-cinnamoyloxy-) showed moderate antineoplastic activity in the case of Colon Cancer, Breast Cancer and Leukemia cell lines.