Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
| Autor: | Guillermo Schmeda-Hirschmann, Mariano Walter Pertino, Erina Petrera, Laura Edith Alche |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Proton Magnetic Resonance Spectroscopy
Drug Evaluation Preclinical Pharmaceutical Science Herpesvirus 1 Human 01 natural sciences Analytical Chemistry Terpene HYBRID MOLECULES purl.org/becyt/ford/1 [https] chemistry.chemical_compound Mice Drug Discovery Organic chemistry CYTOTOXICITY Oleanolic acid chemistry.chemical_classification Ciencias Químicas antiviral Ferruginol Chemistry (miscellaneous) ANTIVIRAL click chemistry Click chemistry Molecular Medicine cytotoxicity CLICK CHEMISTRY CIENCIAS NATURALES Y EXACTAS Spectrometry Mass Electrospray Ionization Alkyne Antineoplastic Agents hybrid molecules Antiviral Agents Article lcsh:QD241-441 lcsh:Organic chemistry Cell Line Tumor purl.org/becyt/ford/1.4 [https] Animals Humans TERPENES Physical and Theoretical Chemistry Carbon-13 Magnetic Resonance Spectroscopy 010405 organic chemistry Terpenes Organic Chemistry Carnosic acid 0104 chemical sciences 010404 medicinal & biomolecular chemistry Química Orgánica RAW 264.7 Cells chemistry Azide Diterpene Drug Screening Assays Antitumor |
| Zdroj: | CONICET Digital (CONICET) Consejo Nacional de Investigaciones Científicas y Técnicas instacron:CONICET Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry Molecules Volume 23 Issue 6 Molecules, Vol 23, Iss 6, p 1343 (2018) |
| Popis: | 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 &gamma 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 1&ndash 16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 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 3&ndash 8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI &ge 10, SI = CC50/CE50) for some compounds. |
| Databáze: | OpenAIRE |
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