A one-pot synthesis and biological activity of ageladine A and analogues

Sudhir R. Shengule, Wendy L. Loa-Kum-Cheung, Christopher R. Parish, Mélina Blairvacq, Laurent Meijer, Yoichi Nakao, Peter Karuso*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)


A one-pot synthesis of ageladine A and analogues is reported. The key Pictet-Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were screened for their matrix metalloprotease (MMP) and kinase inhibition to develop the first structure-activity relationship of ageladine A analogues. One compound, which showed significant kinase activity but little MMP inhibitory activity, was found to be highly active in an antiangiogenic screen, suggesting that the angiogenic activity of ageladine A is not associated with MMP inhibition but rather kinase inhibitory activity. Cytotoxicity was excluded as a mode of action by the assay of ageladine A and an analogue against 60 human cell lines.

Original languageEnglish
Pages (from-to)2492-2503
Number of pages12
JournalJournal of Medicinal Chemistry
Issue number7
Publication statusPublished - 2011 Apr 14

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


Dive into the research topics of 'A one-pot synthesis and biological activity of ageladine A and analogues'. Together they form a unique fingerprint.

Cite this