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- Title
Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry.
- Authors
Pertino, Mariano Walter; Petrera, Erina; Alché, Laura Edith; Schmeda-Hirschmann, Guillermo
- Abstract
Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids <bold>1</bold>–<bold>16</bold> was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds <bold>1</bold>, <bold>2</bold>, <bold>3</bold> and <bold>7</bold> showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds <bold>3</bold>–<bold>8</bold>, except for compound <bold>7</bold>), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.
- Subjects
ANTIVIRAL agents; DITERPENES; ALKYNE derivatives; CARNOSIC acid; LACTONES
- Publication
Molecules, 2018, Vol 23, Issue 6, p1343
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23061343