title: Telescoped Synthesis of 2-Acyl-1-aryl-1,2-dihydroisoquinolines and Their Inhibition of the Transcription Factor NF-κB.
abstract: 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.
authors.forename: Tsai-Wen
authors.initials: TW
authors.lastname: Chung
authors.forename: Yi-Tzu
authors.initials: YT
authors.lastname: Hung
authors.forename: Tushar
authors.initials: T
authors.lastname: Thikekar
authors.forename: Vijaykumar V
authors.initials: VV
authors.lastname: Paike
authors.forename: Fu Yuan
authors.initials: FY
authors.lastname: Lo
authors.forename: Pei-Hua
authors.initials: PH
authors.lastname: Tsai
authors.forename: Mei-Chih
authors.initials: MC
authors.lastname: Liang
authors.affiliation: §Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100 Shih-Chuan First Road, Kaohsiung 807, Taiwan.
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
mesh_terms: D000818:Animals; D002478:Cells, Cultured; D006801:Humans; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors* / Q000378:metabolism; D041681:NIH 3T3 Cells; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: C109853:G 1617; D007546:Isoquinolines; D016328:NF-kappa B; D014409:Tumor Necrosis Factor-alpha
keywords: 3T3 cells; DNA binding; amidealkylation; dihydroisoquinolines; p65 nuclear translocation; transcription factor NF-κB