Benzofuran-derived cyclic beta-amino acid scaffold for building a diverse set of flavonoid-like probes and the discovery of a cell motility inhibitor.
We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC50 approximately 40 microM in chamber cell migration assay).
Nandy
Jyoti P
JP
Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada.
Rakic
Bojana
B
Sarma
Bugga V N B
BV
Babu
Nallareddy
N
Lefrance
Marc
M
Enright
Gary D
GD
Leek
Donald M
DM
Daniel
Kate
K
Sabourin
Luc A
LA
Arya
Prabhat
P
D000598:Amino Acids, Cyclic / Q000737:chemistry*; D000818:Animals; D001572:Benzofurans / Q000737:chemistry*; D002465:Cell Movement / Q000187:drug effects*; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology; D051379:Mice; D015335:Molecular Probes; D041681:NIH 3T3 Cells
D000598:Amino Acids, Cyclic; D001572:Benzofurans; D005419:Flavonoids; D015335:Molecular Probes; C105430:benzofuran