Telescoped Synthesis of 2-Acyl-1-aryl-1,2-dihydroisoquinolines and Their Inhibition of the Transcription Factor NF-κB

Tsai Wen Chung, Yi Tzu Hung, Tushar Thikekar, Vijaykumar V. Paike, Fu Yuan Lo, Pei Hua Tsai, Mei-Chih Liang*, Chung-Ming Sun

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

(Chemical Equation Presented). A sequential single-flask multicomponent reactions is highly effective for the synthesis of 1,2-dihydroisoquinolines through amidealkylation from intermediate N-acylisoquinolinium salts under mild conditions. N-Acylisoquinolinium ions and trichloromethyl-1-(1H-indol-3-yl)isoquinoline-2(1H)-carboxylate have demonstrated their reactivity toward aromatic and aliphatic π-nucleophiles. One of the 1,2-dihydroisoquinoline derivatives was found to be a potent inhibitor for transcription factor NF-κB by blocking IκBα degradation, p65 nuclear translocation, and NF-κB DNA binding in TNF-α-induced NIH 3T3 cells.

Original languageEnglish
Pages (from-to)442-451
Number of pages10
JournalACS Combinatorial Science
Volume17
Issue number8
DOIs
StatePublished - 10 Aug 2015

Keywords

  • 3T3 cells
  • amidealkylation
  • dihydroisoquinolines
  • DNA binding
  • p65 nuclear translocation
  • transcription factor NF-κB

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