Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE 2 production in cells

Breland Smith, Hui Hua Chang, Federico Medda, Vijay Gokhale, Justin Dietrich, Angela Davis, Emmanuelle J. Meuillet, Christopher Hulme

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE 2 in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE 2 reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R 2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R 1 = Me, R 2 = 4-OPh-Ph, R 3 = CH(OH)Me) exhibited the most potent cellular PGE 2 reducing activity of the entire series (EC 50 = 90 nM) with an IC 50 value for COX-2 inhibition of >5 μM in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity.

Original languageEnglish (US)
Pages (from-to)3567-3570
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number10
StatePublished - May 15 2012


  • 2-Aminothiazoles
  • COX-2
  • Colon cancer
  • PGE

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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