Synthesis of ortho-functionalized 4-aminomethylpyridazines as substrate-like semicarbazide-sensitive amine oxidase inhibitors

Norbert Haider, Iris Hochholdinger, Péter Mátyus, Andrea Wobus

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A series of 4-aminomethylpyridazines and -pyridazin-3(2H)-ones ("diaza-benzylamines"), bearing alkylamino side chains in ortho position relative to the CH2NH2 unit, was synthesized by catalytic hydrogenation of the corresponding nitriles in strongly acidic medium. N-Benzyl protecting groups either at the pyridazinone ring nitrogen or at an exocyclic nitrogen were selectively removed hydrogenolytically or by treatment with a Lewis acid. The new compounds were tested in vitro for semicarbazide-sensitive amine oxidase (SSAO) inhibitory activity and 4-(aminomethyl)-N,Ń-diethylpyridazine-3,5-diamine (22) was found to be the most active representative.

Original languageEnglish
Pages (from-to)964-970
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number7
DOIs
Publication statusPublished - Jul 2010

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Keywords

  • 4-Aminomethylpyridazine
  • Diaza-benzylamine
  • Selective debenzylation
  • Semicarbazide-sensitive amine oxidase inhibitor
  • Semicarbazide-sensitive amine oxidase/vascular adhesion protein 1

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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