Synthesis of 30-Amino Derivatives of Lupane Triterpenoids

Published on Nov 1, 2005in Chemistry of Natural Compounds0.809
路 DOI :10.1007/S10600-006-0014-9
N. V. Uzenkova5
Estimated H-index: 5
(RAS: Russian Academy of Sciences),
N. I. Petrenko8
Estimated H-index: 8
(RAS: Russian Academy of Sciences)
+ 2 AuthorsTolstikov Genrikh A29
Estimated H-index: 29
(RAS: Russian Academy of Sciences)
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Abstract
New derivatives of betulin and betulinic acid containing various amines on C-30 that are of interest as potentially biologically active agents were prepared.
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: The plant-derived terpenoids and analogues are reviewed with respect to their anti-HIV activity, structure-activity relationships, and mechanism of action. The active compounds include diterpenoid lactones, phenolic diterpenes, atisane and kaurane diterpenes, phorbol diterpenes, triterpene glycosides, friedelane triterpenes, taraxerane triterpenes, ursane triterpenes, lanostane triterpene, lupane triterpenes, seco-ring A triterpenes, degraded triterpenes, and cucurbitacin triterpenes. Positive...
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Succinyl and 3鈥-substituted glutaryl betulin derivatives showed stronger anti-HIV activity and higher therapeutic index (TI) values than their dihydrobetulin counterparts, with ratios of 1.2:1 to 15:1 (cf. 7 and 15, 9 and 17, 10 and 18, 11 and 19, and 12 and 20). For various 3鈥-substituted glutaryl compounds, the order of anti-HIV effects, from strong to weak inhibition, was 3鈥,3鈥-dimethyl, 3鈥-methyl, 3鈥-ethyl-3鈥-methyl, followed by 3鈥,3鈥-tetramethylene glutaryl derivatives (10 > 9 > 11 > 12, 18...
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The triterpene betulinic acid inhibits the activity of aminopeptidase N (EC 3.4.11.2) in a dose-dependent manner. An IC 50 of 7.3 卤 1.4 渭M was determined for betulinic acid. This inhibitory activity is higher than that of bestatin (IC 50 = 16.9 卤 4.1 渭M), a well known inhibitor of this enzyme. The finding supports the idea that betulinic acid acts as anti-melanoma agent via inhibition of aminopeptidase N activity.
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