ABSTRACT
The synthesis and X-ray diffraction established the structure of (7R,8S)-(see text for symbol)-(13R,17R)-trioxolaneabietic acid. Predicted by the computer system PASS antineoplastic activity and the ability to induce apoptosis, a mechanism of cell death, is correlated with experimentally shown cytotoxic activity against malignant cell line MeWo. Results of tests on animals have shown that abietic acid and its 9R,11S-epoxy-12R,15R-trioxolane derivative have anti-inflammatory and antiulcer activity in the absence of adverse effects on animal organisms.
Subject(s)
Abietanes/chemical synthesis , Abietanes/pharmacology , Abietanes/chemistry , Acetic Acid/toxicity , Animals , Cell Line, Tumor/drug effects , Formaldehyde/toxicity , Humans , Inflammation/chemically induced , Inflammation/drug therapy , Magnetic Resonance Spectroscopy , Mice , Rats , Ulcer/chemically induced , Ulcer/drug therapy , Ulcer/pathology , X-Ray DiffractionABSTRACT
The resolution of the racemic ortho-isobornylphenol into enantiomers via diastereomeric camphanates was carried out. The absolute configuration ofchiral centers of synthesized compounds was established by the single crystal X-ray diffraction method. Antioxidant activity and membrane protective properties of individual enantiomers were studied on the model of H2O2-induced hemolysis of red blood cells.
Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Camphanes/chemical synthesis , Camphanes/pharmacology , Phenols/chemistry , Phenols/pharmacology , Animals , Cell Membrane/drug effects , Crystallography, X-Ray , Erythrocytes/drug effects , Hemoglobins/chemistry , Hemolysis , Hydrogen Peroxide/chemistry , Mice , Oxidation-Reduction , StereoisomerismABSTRACT
Effective synthesis of new olean-18(19)-ene triterpenoids based on interaction of allobetulin or its acetate with phosphorous oxychloride in pyridine under reflux is described. The structures of the synthesized 17-chloromethyl-oleane-18(19)-enes have been established with the help of NMR-spectroscopy and X-Ray analysis.
Subject(s)
Oleanolic Acid/chemical synthesis , Triterpenes/chemistry , Molecular Structure , Oleanolic Acid/chemistryABSTRACT
A new triterpenoid of the germanicane series 3S,19R-diacetoxy-17-iodomethylenoleanane has been synthesized by treating allobetulin with acetyl chloride and sodium iodide in acetonitrile. The structure of the compound obtained has been corroborated by X-ray analysis data.
