Polycyclic N-heterocyclic compounds. Part 64: Synthesis of 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and related compounds. Evaluation of their bronchodilator activity and effects on lipoprotein lipase mRNA expression

Kensuke Okuda, Hiroshi Deguchi, Setsuo Kashino, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Reaction of 1-(3-cyanopropoxy)-3,4-dihydronaphthalene-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c] isoquinolines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the bromo derivatives which were allowed to react with aliphatic cyclic amines to produce amino derivatives. In contrast, a combination of imidazole and NaH gave a dihydrofuran ring cleaved product, the structure of which was confirmed by X-ray crystallographic analysis. Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator.

Original languageEnglish
Pages (from-to)685-689
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number5
DOIs
Publication statusPublished - May 1 2010

Keywords

  • Bronchodilator activity
  • Cyclization
  • Furo[2,3-b]pyridine
  • Lipoprotein lipase
  • Ring cleavage
  • Truce-Smiles rearrangement

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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