Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds
authors Sousa, JLC; Freire, CSR; Silvestre, AJD; Silva, AMS
nationality International
journal MOLECULES
author keywords triterpenes; betulinic acid; betulin; betulonic acid; 23-hydroxybetulinic acid; synthesis; functionalization; derivatization
keywords PENTACYCLIC TRITERPENE DERIVATIVES; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY; LUPANE TRITERPENOIDS; CYTOTOXIC EVALUATION; IN-VITRO; MATURATION INHIBITOR; DESIGN; ESTERS; HYBRIDS
abstract 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 polymerBA 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.
publisher MDPI
issn 1420-3049
year published 2019
volume 24
issue 2
digital object identifier (doi) 10.3390/molecules24020355
web of science category Biochemistry & Molecular Biology; Chemistry, Multidisciplinary
subject category Biochemistry & Molecular Biology; Chemistry
unique article identifier WOS:000457137200141
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  impact metrics
journal analysis (jcr 2017):
journal impact factor 3.098
5 year journal impact factor 3.268
category normalized journal impact factor percentile 57.994
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