Rhazinilam

Rhazinilam

Names
IUPAC name (3aR)-3a-Ethyl-2,3,3a,4,5,7-hexahydroindolizino[8,1-ef][1]benzazonin-6(1H)-one
Identifiers
CAS Number	36193-36-9 N
3D model (JSmol)	Interactive image
ChemSpider	9487402 Y
PubChem CID	11312435
InChI InChI=1S/C19H22N2O/c1-2-19-10-5-12-21-13-9-15(18(19)21)14-6-3-4-7-16(14)20-17(22)8-11-19/h3-4,6-7,9,13H,2,5,8,10-12H2,1H3,(H,20,22)/t19-/m1/s1 Y Key: VLQAFTDOIRUYSZ-LJQANCHMSA-N Y InChI=1S/C19H22N2O/c1-2-19-10-5-12-21-13-9-15(18(19)21)14-6-3-4-7-16(14)20-17(22)8-11-19/h3-4,6-7,9,13H,2,5,8,10-12H2,1H3,(H,20,22)/t19-/m1/s1 Key: VLQAFTDOIRUYSZ-LJQANCHMSA-N
SMILES CC[C@]12CCCN3C1=C(C=C3)C4=CC=CC=C4NC(=O)CC2
Properties
Chemical formula	C19H22N2O
Molar mass	294.40 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

See also

• Pyrrole

References

1. ↑ 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. 
2. ↑ 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. 
3. ↑ Bowie, Alfred L.; Hughes, Chambers C.; Trauner, Dirk. "Concise Synthesis of (±)-Rhazinilam through Direct Coupling". Organic Letters. 7 (23): 5207–5209. PMID 16268539. doi:10.1021/ol052033v.