Triazolyl tryptoline derivatives as β-secretase inhibitors

Jutamas Jiaranaikulwanitch, Chantana Boonyarat, Valery V. Fokin, Opa Vajragupta

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Tryptoline, a core structure of ochrolifuanine E, which is a hit compound from virtual screening of the Thai herbal database against BACE1 was used as a scaffold for the design of BACE1 inhibitors. The tryptoline was linked with different side chains by 1,2,3-triazole ring readily synthesized by catalytic azide-alkyne cycloaddition reactions. Twenty two triazolyl tryptoline derivatives were synthesized and screened for the inhibitory action against BACE1. JJCA-140 was the most potent inhibitor (IC50 = 1.49 μM) and was 100 times more selective for BACE1 than for Cat-D.

Original languageEnglish
Pages (from-to)6572-6576
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number22
DOIs
Publication statusPublished - 15 Nov 2010
Externally publishedYes

Keywords

  • BACE1
  • BACE1 inhibitor
  • Binding mode
  • Cathepsin-D
  • Docking
  • Enzyme assay
  • JJCA-140
  • Tryptoline

ASJC Scopus subject areas

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

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  • Cite this

    Jiaranaikulwanitch, J., Boonyarat, C., Fokin, V. V., & Vajragupta, O. (2010). Triazolyl tryptoline derivatives as β-secretase inhibitors. Bioorganic and Medicinal Chemistry Letters, 20(22), 6572-6576. https://doi.org/10.1016/j.bmcl.2010.09.043