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 ;
3D model (JSmol)	Interactive image;
ChemSpider	9487402 ;
PubChem CID	11312435;
CompTox Dashboard (EPA)	DTXSID90957594 ;
	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 Key: VLQAFTDOIRUYSZ-LJQANCHMSA-N ; 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	294.398 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 the shrub Rhazya stricta as well as from other organisms.

Biological activity

Rhazinilam has activity similar to that of colchicine, taxol and vinblastine, acting as a spindle poison.[1]

Total synthesis

Rhazinilam was first synthesized in 1973 by Smith and coworkers, and multiple subsequent times.[2]

Trauner synthesis

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. PMID 16268539.

Rhazinilam – Trauner synthesis

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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.

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[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.