Total synthesis and cytotoxicity of Leucetta alkaloids

Bioorg Med Chem. 2017 Mar 1;25(5):1608-1621. doi: 10.1016/j.bmc.2017.01.024. Epub 2017 Jan 20.

Abstract

The total synthesis of a number of representative natural products isolated from Leucetta and Clathrina sponges containing a polysubstituted 2-aminoimidazole are described. These syntheses take advantage of the site specific metallation reactions of 4,5-diiodoimidazoles resulting in the syntheses of three different classes of Leucetta derived natural products. The cytotoxicities of these natural products, along with several precursors in MCF7 cells were determined through an MTT growth assay. For comparative purposes a series of naphthimidazole-containing family members are included.

Keywords: 2-Aminoimidazole; Heterocycles; Metallation; Naphthimidazole; Reduction.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Animals
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Female
  • Humans
  • MCF-7 Cells
  • Porifera
  • Spectrum Analysis / methods
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Biological Products