Synthesis and acetylcholinesterase/butyrylcholinesterase inhibition activity of 4-amino-2,3-diaryl- 5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]-quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridines

José L. Marco, Cristóbal De Los Ríos, María C. Carreiras, Josep E. Baños, Albert Badia, Nuria M. Vivas

Research output: Contribution to journalArticleResearchpeer-review

27 Citations (Scopus)

Abstract

The acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition activities of a series of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro[2,3-b]quinolines (10-12)/4-amino-5,6,7,8-tetrahydro-2,3-diphenylthieno[2,3-b]quinoline (14) and 4- amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo[2,3-b]pyridine (13)/4- amino-5,6,7,8,9-pentahydro-2,3-phenylcyclohepta[e]thieno[2,3-b]pyridine (15) are described. These compounds are tacrine (THA) analogues which have been prepared either from readily available 2-amino-3-cyano-4,5-diarylfurans (16-18) or from 2-amino-3-cyano-4,5-diphenylthiophene (19), via Friedländer condensation with cyclohexanone or cycloheptanone. These compounds are competitive inhibitors for acetylcholinesterase, the more potent being compound (13) which is threefold less active than tacrine. The butyrylcholinesterase inhibition activity is significant only in compounds 10 and 13, which are ten-fold less active than tacrine. It is found that the products 11 and 12 strongly inhibit acetylcholinesterase, and show excellent selectivity regarding butyrylcholinesterase.
Original languageEnglish
Pages (from-to)347-353
JournalArchiv der Pharmazie
Volume335
Issue number7
DOIs
Publication statusPublished - 1 Jul 2002

Keywords

  • AChE/BuChE inhibitors
  • Furo[2,3-b]quinolines
  • Tacrine analogues
  • Thieno[2,3-b]quinolines

Fingerprint Dive into the research topics of 'Synthesis and acetylcholinesterase/butyrylcholinesterase inhibition activity of 4-amino-2,3-diaryl- 5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]-quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridines'. Together they form a unique fingerprint.

  • Cite this