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Molecules 2018, 23(6), 1343; https://doi.org/10.3390/molecules23061343

Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

1
Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, 3460000 Talca, Chile
2
Programa de Investigación de Excelencia Interdisciplinaria en Química y Bio-orgánica de Recursos Naturales (PIEI-QUIM-BIO), Universidad de Talca, 3460000 Talca, Chile
3
Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428BGA Buenos Aires, Argentina
4
Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales (IQUIBICEN), CONICET—Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
*
Author to whom correspondence should be addressed.
Received: 17 May 2018 / Revised: 1 June 2018 / Accepted: 1 June 2018 / Published: 3 June 2018
(This article belongs to the Special Issue Natural Product Pharmacology and Medicinal Chemistry)
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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 116 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 38, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds. View Full-Text
Keywords: hybrid molecules; terpenes; antiviral; cytotoxicity; click chemistry hybrid molecules; terpenes; antiviral; cytotoxicity; click chemistry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Pertino, M.W.; Petrera, E.; Alché, L.E.; Schmeda-Hirschmann, G. Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry. Molecules 2018, 23, 1343.

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