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Chemical Compound Review: 

Necic acid     (2R,3R,5Z)-5-ethylidene-2- hydroxy-2,3...

Synonyms: AC1O5UBF, 13588-16-4
 
 
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High impact information on Necic acid

  • In the heliotridine series, the configuration of the necic acid has a pronounced effect on the site selectivity (C-7 vs C-9) in esterification with carbodiimidazole [1].
  • 2. The dehydroalkaloids are highly reactive and either bind covalentely to tissue nucleophiles or are hydrolysed to the more stable pyrrole, (R,S)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP), and the corresponding necic acid [2].
 

Associations of Necic acid with other chemical compounds

  • Firstly, the necine bases are structurally modified and either before or after this modification are converted into their O(9)-esters by esterification with one of the stereoisomers of 2,3-dihydroxy-2-isopropylbutyric acid, the unique necic acid of PAs of the lycopsamine type [3].

References

  1. Semisynthetic pyrrolizidine alkaloid N-oxide antitumor agents. Esters of heliotridine. Zalkow, L.H., Glinski, J.A., Gelbaum, L.T., Moore, D., Melder, D., Powis, G. J. Med. Chem. (1988) [Pubmed]
  2. Microsomal formation of a pyrrolic alcohol glutathione conjugate of the pyrrolizidine alkaloid senecionine. Reed, R.L., Miranda, C.L., Kedzierski, B., Henderson, M.C., Buhler, D.R. Xenobiotica (1992) [Pubmed]
  3. Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. Frölich, C., Ober, D., Hartmann, T. Phytochemistry (2007) [Pubmed]
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