Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds

Betulinic acid (BA) and its natural analogues betulin (BN), betulonic (BoA), and 23-hydroxybetulinic (HBA) acids are lupane-type pentacyclic triterpenoids. They are present in many plants and display important biological activities. This review focuses on the chemical transformations used to functio...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-01, Vol.24 (2), p.355
Main Authors: Sousa, Joana L C, Freire, Carmen S R, Silvestre, Armando J D, Silva, Artur M S
Format: Article
Language:English
Subjects:
23-hydroxybetulinic acid
Acids
Aldehydes
Alkylation
Alkynes
Amination
Antimalarial activity
Antimalarial agents
betulin
Betulinic acid
betulonic acid
Bioactive compounds
Biological activity
Cancer
Chemical reactions
Chloride
Cross coupling
Cycloaddition
Cytotoxicity
derivatization
Drug delivery
Drug resistance
Esterification
functionalization
HIV
Human immunodeficiency virus
Hydroxylation
Medical imaging
Methods
Palladium
Pentacyclic triterpenoids
Polymers
Review
Sulfonation
synthesis
triterpenes
Triterpenoids
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Summary:Betulinic acid (BA) and its natural analogues betulin (BN), betulonic (BoA), and 23-hydroxybetulinic (HBA) acids are lupane-type pentacyclic triterpenoids. They are present in many plants and display important biological activities. This review focuses on the chemical transformations used to functionalize BA/BN/BoA/HBA in order to obtain new derivatives with improved biological activity, covering the period since 2013 to 2018. It is divided by the main chemical transformations reported in the literature, including amination, esterification, alkylation, sulfonation, copper(I)-catalyzed alkyne-azide cycloaddition, palladium-catalyzed cross-coupling, hydroxylation, and aldol condensation reactions. In addition, the synthesis of heterocycle-fused BA/HBA derivatives and polymer‒BA conjugates are also addressed. The new derivatives are mainly used as antitumor agents, but there are other biological applications such as antimalarial activity, drug delivery, bioimaging, among others.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24020355