Rhazinilam
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| Preferred IUPAC name
(3aR)-3a-Ethyl-2,3,3a,4,5,7-hexahydroindolizino[8,1-ef][1]benzazonin-6(1H)-one | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C19H22N2O | |
| Molar mass | 294.398 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rhazinilam is an alkaloid first isolated in 1965 by Linde from the Melodinus australis plant. It was later isolated from the shrub Rhazya stricta as well as from other organisms.
Biological activity
[edit]Rhazinilam has activity similar to that of colchicine, taxol and vinblastine, acting as a spindle poison.[1]
Total synthesis
[edit]Rhazinilam was first synthesized in 1973 by Smith and coworkers, and multiple subsequent times.[2]
Trauner synthesis
[edit]Bowie, Alfred L.; Hughes, Chambers C.; Trauner, Dirk (2005). "Concise Synthesis of (±)-Rhazinilam through Direct Coupling". Organic Letters. 7 (23): 5207–5209. doi:10.1021/ol052033v. PMID 16268539.
Rhazinilam – Trauner synthesis
References
[edit]- ↑ David, Bruno; Sévenet, Thierry; Thoison, Odile; Awang, Khalijah; Païs, Mary; Wright, Michel; Guénard, Daniel (1997). "Hemisynthesis of rhazinilam analogues: structure - activity relationships on tubulin-microtubule system". Bioorganic & Medicinal Chemistry Letters. 7 (17): 2155–2158. doi:10.1016/S0960-894X(97)00391-0.
- ↑ Ratcliffe, A.H.; Smith, G.F.; Smith, G.N. (1973). "The synthesis of rhazinilam". Tetrahedron Letters. 14 (52): 5179–5184. doi:10.1016/S0040-4039(01)87657-7.