Synthesis and cytotoxicity of allobetulin derivatives

A variety of oxygen-, nitrogen-, sulfur-, and platinum-containing allobetulin derivatives, including those with different positions of double bonds in rings A and B, the penta- and hexacyclic ring A, and the 21-acetyl-20,28-epoxy-18α,19βH-ursanoisomeric cycle E, have been synthesized, and the screen...

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Published inRussian journal of bioorganic chemistry Vol. 40; no. 5; pp. 558 - 567
Main Authors Kazakova, O. B., Smirnova, I. E., Khusnutdinova, E. F., Zhukova, O. S., Fetisova, L. V., Apryshko, G. N., Medvedeva, N. I., Yamansarov, E. Yu, Baikova, I. P., Nguyen, Thanh Tra, Thu, H. Do Thi
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.09.2014
Subjects
Biochemistry
Biomedical and Life Sciences
Biomedicine
Bioorganic Chemistry
Life Sciences
Organic Chemistry
synthesis
allobetulin
triterpenoids
cytotoxicity
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Summary:A variety of oxygen-, nitrogen-, sulfur-, and platinum-containing allobetulin derivatives, including those with different positions of double bonds in rings A and B, the penta- and hexacyclic ring A, and the 21-acetyl-20,28-epoxy-18α,19βH-ursanoisomeric cycle E, have been synthesized, and the screening of their antineoplastic activity in vitro (cytotoxicity) has been carried out. A significant cytotoxic activity was exhibited by (3 R ,5 R )-19β,28-epoxy-4,5-seco-18α-olean-3(5)-ozonide toward MeWo melanoma cells and by 2,3-indolo-21β-acetyl-20β,28-epoxy-18α,19βH-ursane toward SR leukosis cells. The 3 S ,5 S -diastereoisomer of the former compound showed no cytotoxicity.
ISSN:1068-1620
1608-330X
DOI:10.1134/S1068162014050082