Concise syntheses of the abyssinones and discovery of new inhibitors of prostate cancer and MMP-2 expression

Rebecca L. Farmer, Margaret M. Biddle, Antoinette E. Nibbs, Xiaoke Huang, Raymond C. Bergan, Karl A. Scheidt

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

The first asymmetric syntheses of four members of the abyssinone class of natural products (I, II, III, and IV 4′-OMe) via quinine- or quinidine-derived thiourea-catalyzed intramolecular conjugate additions of β-keto ester alkylidenes are reported. This concise strategy delivers all four natural products and their corresponding antipodes. A preliminary evaluation of all of these small molecules against a metastatic human prostate cancer cell line has identified that these compounds selectively and differentially inhibit cell growth and downregulate the expression of matrix metalloproteinase-2 (MMP-2) at nontoxic concentrations.

Original languageEnglish (US)
Pages (from-to)400-405
Number of pages6
JournalACS Medicinal Chemistry Letters
Volume1
Issue number8
DOIs
StatePublished - Nov 11 2010

Keywords

  • Abyssinones
  • MMP-2 expression
  • hydrogen-bonding catalysis
  • prostate cancer

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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