[Synthesis and cytotoxicity of triterpenoid seven members cyclic amines].

Publisher: Nauka Country of Publication: Russia (Federation) NLM ID: 7804941 Publication Model: Print Cited Medium: Print ISSN: 0132-3423 (Print) Linking ISSN: 01323423 NLM ISO Abbreviation: Bioorg Khim Subsets: MEDLINE

Original Publication: Moskva, Nauka

Structure-Activity Relationship*; Neoplasms/*drug therapy ; Oleanolic Acid/*analogs & derivatives ; Triterpenes/*chemical synthesis; 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/pathology ; Oleanolic Acid/chemical synthesis ; Oleanolic Acid/chemistry ; Triterpenes/chemistry

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.

0 (Antineoplastic Agents)
0 (Antiviral Agents)
0 (Triterpenes)
0 (oleanonic acid)
3VWF903FSS (erythrodiol)
6SMK8R7TGJ (Oleanolic Acid)
6W70HN7X7O (betulin)
PJY633525U (Adamantane)

Date Created: 20150422 Date Completed: 20150603 Latest Revision: 20191027

20231215

10.1134/s106816201402006x

25895342