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De novo synthesis and biological evaluation of C6?-substituted C4?-amide analogues of SL0101.

ABSTRACT: In an effort to improve upon the in vivo half-life of the known ribosomal s6 kinase (RSK) inhibitor SL0101, C4?-amide/C6?-alkyl substituted analogues of SL0101 were synthesized and evaluated in cell-based assays. The analogues were prepared using a de novo asymmetric synthetic approach, which featured Pd-?-allylic catalyzed glycosylation for the introduction of a C4?-azido group. Surprisingly replacement of the C4?-acetate with a C4?-amide resulted in analogues that were no longer specific for RSK in cell-based assays.

SUBMITTER: Mrozowski RM 

PROVIDER: S-EPMC4251525 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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De novo synthesis and biological evaluation of C6″-substituted C4″-amide analogues of SL0101.

Mrozowski Roman M RM   Sandusky Zachary M ZM   Vemula Rajender R   Wu Bulan B   Zhang Qi Q   Lannigan Deborah A DA   O'Doherty George A GA  

Organic letters 20141105 22

In an effort to improve upon the in vivo half-life of the known ribosomal s6 kinase (RSK) inhibitor SL0101, C4″-amide/C6″-alkyl substituted analogues of SL0101 were synthesized and evaluated in cell-based assays. The analogues were prepared using a de novo asymmetric synthetic approach, which featured Pd-π-allylic catalyzed glycosylation for the introduction of a C4″-azido group. Surprisingly replacement of the C4″-acetate with a C4″-amide resulted in analogues that were no longer specific for R  ...[more]

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