Bioorganic & medicinal chemistry letters, 2011-05, Vol.21 (10), p.2930-2933
2011
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- Autor(en) / Beteiligte
- Titel
- Total synthesis of solamargine
- Ist Teil von
- Bioorganic & medicinal chemistry letters, 2011-05, Vol.21 (10), p.2930-2933
- Ort / Verlag
- Amsterdam: Elsevier Ltd
- Erscheinungsjahr
- 2011
- Quelle
- MEDLINE
- Beschreibungen/Notizen
- Solamargine has been synthesized in 13 steps and 10.5% overall yield from the natural abundant diosgenin. Solamargine, (25 R)-3β-{ O-α- l-rhamnopyranosyl-(1→2)-[ O-α- l-rhamnopyranosyl-(1→4)]-β- d-glucopyranosyloxy}-22α- N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC 50 ranging from 2.1 to 8.0 μM.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 0960-894XeISSN: 1464-3405DOI: 10.1016/j.bmcl.2011.03.064Titel-ID: cdi_proquest_miscellaneous_874193376
- Format
- –
- Schlagworte
- Antineoplastic agents, Antineoplastic Agents - chemical synthesis, Antineoplastic Agents - chemistry, Antineoplastic Agents - pharmacology, Biological and medical sciences, Cell Line, Tumor, Cell Survival - drug effects, condensation, Cytotoxic activity, cytotoxicity, diosgenin, Diosgenin - chemistry, General aspects, Glycosides, Humans, Inhibitory Concentration 50, Medical sciences, Molecular Structure, Natural products, Pharmacology. Drug treatments, Solamargine, Solanaceous Alkaloids - chemical synthesis, Solanaceous Alkaloids - chemistry, Solanaceous Alkaloids - pharmacology, Solasodine