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Chemical Compound Review

NSC326672     (5S)-3-[(2R,13R)-2,13- dihydroxy-13-[(5S)-5...

Synonyms: AC1NS1MQ, Rolliniastatin 1
 
 
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High impact information on NSC326672

  • A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3) [1].
  • The most active compound was Rolliniastatin 1 (IC50 at 4.7 microM) [2].
  • Among them, the adjacent bis-tetrahydrofuranic acetogenins (bis-THF ACG) with a threo/cis/threo/cis/erythro relative configuration, have been described as the most potent subgroup, the prototypical member of which, rolliniastatin-1, was originally isolated from Rollinia membaranacea seeds [3].

References

  1. Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin. Keum, G., Hwang, C.H., Kang, S.B., Kim, Y., Lee, E. J. Am. Chem. Soc. (2005) [Pubmed]
  2. In vitro antileishmanial activity of acetogenins from Annonaceae. Raynaud-Le Grandic, S., Fourneau, C., Laurens, A., Bories, C., Hocquemiller, R., Loiseau, P.M. Biomed. Pharmacother. (2004) [Pubmed]
  3. In vitro antitumor SAR of threo/cis/threo/cis/erythro bis-THF acetogenins: correlations with their inhibition of mitochondrial Complex I. Royo, I., DePedro, N., Estornell, E., Cortes, D., Peláez, F., Tormo, J.R. Oncol. Res. (2003) [Pubmed]
 
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