Modification in pentacyclic triterpene structures is a frequent and interesting chemical approach in order to improve biological potential of those analogues, when compared to natural triterpenes. Celastraceae species are well-known for their abundance in natural pentacyclic triterpenes, therefore triterpene-rich plants can be used as sources of those compounds for posterior synthetic modifications. Cheiloclinium cognatum, commonly known as bacupari da mata, is a Celastraceae species found in Brazilian Cerrado biome. It is used in traditional medicine to treat edema and fever. Pentacyclic triterpenes isolated from C. cognatum exhibited analgesic, antiangiogenic, anti-inflammatory, antioxidant and trypanocidal activities. A mixture of the friedelane triterpenes 29-hydroxyfriedelan-3-one and friedelane-3β,29-diol was obtained in great yield from leaf chloroform extract, corresponding about 20% of the total amount. Due to the abundance of these natural products, chemical modifications were carried out in order to enhance their biological potentials. In this work, ten analogues of 29-hydroxyfriedelan-3-one (1) were synthesized as carboxylic acids, esters, lactones, lactames, oximes and/or O-acetyloximes derivatives. The analogues (2-11) (Figure 1) were characterized by their IR, 1D and 2D NMR spectra. Using the KNIME package, the physicochemical properties of the derivatives were calculated to predict the drug and lead-like potentials, based on Lipinski’s “RO5” and Veber’s rules. Additionally, the PreADME and ProToxII webservers were used to predict the pharmacokinetic and toxicological properties. The bacterial growth inhibition activity of the triterpenes was evaluated using broth microdilution assay against E. coli, S. aureus and MRSA. After the screening assay, 11 showed growth inhibition against S. aureus and MRSA at 100 µM and 9 showed partial growth inhibition against MRSA. Both will be investigated by further biological assays. None of the substances showed activity against E. coli. 

Synthesis and antibacterial evaluation of 29-hydroxyfriedelan-3-one derivatives

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.