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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 1–16 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 3–8, 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. © 2018 by the authors.

Registro:

Documento: Artículo
Título:Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
Autor:Pertino, M.W.; Petrera, E.; Edith Alché, L.; Schmeda-Hirschmann, G.
Filiación:Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Talca, 3460000, Chile
Programa de Investigación de Excelencia Interdisciplinaria en Química y Bio-orgánica de Recursos Naturales (PIEI-QUIM-BIO), Universidad de Talca, Talca, 3460000, Chile
Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, C1428BGA, Argentina
Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales (IQUIBICEN), CONICET—Universidad de Buenos Aires, Buenos Aires, C1428EGA, Argentina
Palabras clave:Antiviral; Click chemistry; Cytotoxicity; Hybrid molecules; Terpenes; antineoplastic agent; antivirus agent; terpene; animal; carbon nuclear magnetic resonance; chemistry; click chemistry; drug effect; drug screening; electrospray mass spectrometry; human; Human alphaherpesvirus 1; mouse; preclinical study; proton nuclear magnetic resonance; RAW 264.7 cell line; synthesis; tumor cell line; Animals; Antineoplastic Agents; Antiviral Agents; Carbon-13 Magnetic Resonance Spectroscopy; Cell Line, Tumor; Click Chemistry; Drug Evaluation, Preclinical; Drug Screening Assays, Antitumor; Herpesvirus 1, Human; Humans; Mice; Proton Magnetic Resonance Spectroscopy; RAW 264.7 Cells; Spectrometry, Mass, Electrospray Ionization; Terpenes
Año:2018
Volumen:23
Número:6
DOI: http://dx.doi.org/10.3390/molecules23061343
Título revista:Molecules
Título revista abreviado:Molecules
ISSN:14203049
CODEN:MOLEF
CAS:Antineoplastic Agents; Antiviral Agents; Terpenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14203049_v23_n6_p_Pertino

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Citas:

---------- APA ----------
Pertino, M.W., Petrera, E., Edith Alché, L. & Schmeda-Hirschmann, G. (2018) . Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry. Molecules, 23(6).
http://dx.doi.org/10.3390/molecules23061343
---------- CHICAGO ----------
Pertino, M.W., Petrera, E., Edith Alché, L., Schmeda-Hirschmann, G. "Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry" . Molecules 23, no. 6 (2018).
http://dx.doi.org/10.3390/molecules23061343
---------- MLA ----------
Pertino, M.W., Petrera, E., Edith Alché, L., Schmeda-Hirschmann, G. "Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry" . Molecules, vol. 23, no. 6, 2018.
http://dx.doi.org/10.3390/molecules23061343
---------- VANCOUVER ----------
Pertino, M.W., Petrera, E., Edith Alché, L., Schmeda-Hirschmann, G. Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry. Molecules. 2018;23(6).
http://dx.doi.org/10.3390/molecules23061343