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Rhazinilam

From Wikipedia, the free encyclopedia
Rhazinilam
Names
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)
ChemSpider
  • 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 checkY
    Key: VLQAFTDOIRUYSZ-LJQANCHMSA-N checkY
  • 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
  • CC[C@]12CCCN3C1=C(C=C3)C4=CC=CC=C4NC(=O)CC2
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 the shrub Rhazya stricta as well as from other organisms.

Biological activity

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

Total synthesis

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

Trauner synthesis

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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
Rhazinilam – Trauner synthesis

References

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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.