Rhazinilam
| |
| Names | |
|---|---|
| IUPAC name
(3aR)-3a-Ethyl-2,3,3a,4,5,7-hexahydroindolizino[8,1-ef][1]benzazonin-6(1H)-one
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| 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).
| |
Rhazinilam is an alkaloid first isolated in 1965 by Linde from the Melodinus australis plant. It was later isolated from Rhazya stricta as well as from other sources.
Biological activity
Rhazinilam has activity similar to that of colchicine, taxol and vinblastine, acting as an inhibitor of the tubulin-microtubules equilibrium.[1]
Total synthesis
Rhazinilam was first synthesized in 1973 by Smith and coworkers, and multiple subsequent times.[2]
Trauner synthesis
Rhazinilam was synthesized by the Trauner group in 2005.[3]
Rhazinilam – Trauner synthesis
See also
References
- ^ David, Bruno; Sévenet, Thierry; Thoison, Odile; Awang, Khalijah; Païs, Mary; Wright, Michel; Guénard, Daniel. "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. "The synthesis of rhazinilam". Tetrahedron Letters. 14 (52): 5179–5184. doi:10.1016/S0040-4039(01)87657-7.
- ^ Bowie, Alfred L.; Hughes, Chambers C.; Trauner, Dirk. "Concise Synthesis of (±)-Rhazinilam through Direct Coupling". Organic Letters. 7 (23): 5207–5209. doi:10.1021/ol052033v.