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Syntheses of tricyclic pyrones and pyridinones and protection of Abeta-peptide induced MC65 neuronal cell death.

Abstract：

:The SbetaC gene is conditionally expressed a 99-residue carboxy terminal fragment, C99, of amyloid precursor protein in MC65 cells and causes cell death. Consequently, MC65 cell line was used to identify inhibitors of toxicity related to intracellular amyloid beta (Abeta) oligomers. Compounds that reduce the level of Abeta peptides, prevent Abeta aggregation, or eliminate existing Abeta aggregates may be used in the treatment of Alzheimer's disease (AD). Previously, we found that a tricyclic pyrone (TP) molecule, compound 1, prevents MC65 cell death and inhibits Abeta aggregation. Hence various TPs containing heterocycle at C7 side chain and a nitrogen at position 2 or 5 were synthesized and their MC65 cell protective activities evaluated. TPs containing N3'-adenine moiety such as compounds 1 and 11 are most active with EC(50) values of 0.31 and 0.35 microM, respectively. EC(50) values of tricyclic N5-analog, pyranoisoquinolinone 13, and N2-analog, pyranopyridinone 20, are 2.49 and 1.25 microM, respectively, despite the lack of adenine moiety. Further investigation of tricyclic N2- and N5-analogs is warranted.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Rana S,Hong HS,Barrigan L,Jin LW,Hua DH

doi

10.1016/j.bmcl.2008.12.060

subject

Has Abstract

pub_date

2009-02-01 00:00:00

pages

670-4

issue

3

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(08)01564-3

journal_volume

19

pub_type

杂志文章

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