Synthesis of intermediate derivatives from Schweinfurthin G using chiral ionic liquid
Keywords:schweinfurthin G derivatives, stilbene, Dess-Martin periodinane oxidation, selenium dioxide oxidation, ionic liquid
Schweinfurthins possess a wide diversity of important biological and pharmacological activities. To date, more than fifty schweinfurthins and their analogues have been prepared for the investigation of structure-function relationships. Schweinfurthin G, one of the most representative of schweinfurthins containing the hexahydroxanthene moiety, was found to strongly inhibit the growth of cancer cell lines when evaluated on the U87 cell line (EC50 of 0.04 µM), and on the KB cell line (IC50 of 0.06 µM). Ionic liquids have been regarded as “solvents of the future” and applied in various fields. They have been utilized most widely in modern organic synthesis as an environmentally friendly alternative to conventional organic solvents and catalysts due to their flexible, nonvolatile, noncorrosive, low viscous properties and they still maintain similar and sometimes enhanced chemical selectivity and reactivity of organic reactions. In this paper, we present the synthesis of intermediate compounds 2 and 3, which are the key compounds for synthesizing the derivatives of schweinfurthin G using chiral ionic liquid. These compounds are the key blocks to further synthesize schweinfurthin G derivatives for biological activity tests.
Beutler J. A., Shoemaker R. H., Johnson T., Boyd M. R. - Cytotoxic geranyl stilbenes from Macaranga schweinfurthii, J. Nat. Prod. 61 (12) (1998) 1509-1512. https://doi.org/10.1021/np980208m. https://doi.org/10.1021/np980208m.">
Yoder B. J., Cao S., Norris A., Miller J. S., Ratovoson F., Razafitsalama J., Andriantsiferana R., Rasamison V. E., Kingston D. G. - Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest, J. Nat. Prod. 70 (3) (2007) 342-346. https://doi.org/10.1021/np060484y. https://doi.org/10.1021/np060484y.">
Péresse T., Jézéquel G. L., Allard P.M., Pham V.C., Huong D. T., Blanchard F., Bignon J. R. M., Lévaique H. L. N., Wolfender J.L., Litaudon M. - Cytotoxic prenylated stilbenes isolated from Macaranga tanarius, J. Nat. Prod. 80 (10) (2017) 2684-2691. https://doi.org/10.1021/acs.jnatprod.7b00409. https://doi.org/10.1021/acs.jnatprod.7b00409.">
Harmalkar D. S., Mali J. R., Sivaraman A., Choi Y., Lee K. - Schweinfurthins A–Q: isolation, synthesis, and biochemical properties, RSC Advances 8 (38) (2018) 21191-21209. https://doi.org/10.1039/C8RA02872A. https://doi.org/10.1039/C8RA02872A.">
Kodet J. G., Wiemer D. F. - Synthesis of indole analogues of the natural schweinfurthins, J. Org. Chem. 78 (18) (2013) 9291-9302. https://doi.org/10.1021/jo4014244. https://doi.org/10.1021/jo4014244.">
Neighbors J. D., Beutler J. A., Wiemer D. F. - Synthesis of nonracemic 3-deoxyschweinfurthin B, J. Org. Chem. 70 (3) (2005) 925-931. https://doi.org/10.1021/jo048444r. https://doi.org/10.1021/jo048444r.">
Beutler J. A., Jato J. G., Cragg G., Wiemer D. F., Neighbors J. D., Salnikova M., Hollingshead M., Scudiero D. A., McCloud T. G. - The schweinfurthins: issues in the development of a plant-derived anticancer lead, Frontis, Springer publisher, 2006, 301-309.
Ulrich N. C., Kodet J. G., Mente N. R., Kuder C. H., Beutler J. A., Hohl R. J., Wiemer D. F. - Structural analogues of schweinfurthin F: probing the steric, electronic, and hydrophobic properties of the D-ring substructure, Bioorg. Med. Chem. 18 (4) (2010) 1676-1683. https://doi.org/10.1016/j.bmc.2009.12.063. https://doi.org/10.1016/j.bmc.2009.12.063.">
Topczewski J. J., Callahan M. P., Kodet J. G., Inbarasu J. D., Mente N. R., Beutler J. A., Wiemer D. F. - Relevance of the C-5 position to schweinfurthin induced cytotoxicity, Bioorg. Med. Chem. 19 (24) (2011) 7570-7581. https://doi.org/10.1016/ j.bmc.2011.10.034. https://doi.org/10.1016/ j.bmc.2011.10.034.">
Neighbors J. D., Salnikova M. S., Beutler J. A., Wiemer D. F. - Synthesis and structure–activity studies of schweinfurthin B analogs: evidence for the importance of a D-ring hydrogen bond donor in expression of differential cytotoxicity, Bioorg. Med. Chem. 14 (6) (2006) 1771-1784. https://doi.org/10.1016/j.bmc.2005.10.025. https://doi.org/10.1016/j.bmc.2005.10.025.">
Huong D. T. M., Linh N. T., Van T. T. T., Litaudon M., Roussi F., Van N. V., Van C. P. - Stilbenes from Macaranga tanarius (Euphorbiaceae) growing in Vietnam, Vietnam Journal of Chemistry 58 (3) (2020) 338-342. https://doi.org/10.1002/vjch.2019000182. https://doi.org/10.1002/vjch.2019000182.">
Mente N. R., Neighbors J. D., Wiemer D. F. - BF3· Et2O-mediated cascade cyclizations: Synthesis of schweinfurthins F and G, J. Org. Chem. 73 (20) (2008) 7963-7970. https://doi.org/10.1021/jo800951q. https://doi.org/10.1021/jo800951q.">
Kaur G., Kumar H., Singla M. J. - Diverse applications of ionic liquids: A comprehensive review, J. Mol. Liq. 351 (2022) 118556. https://doi.org/10.1016/j.molliq.2022.118556. https://doi.org/10.1016/j.molliq.2022.118556.">
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