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  • Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part II. Identification of the 1,3,8-triazaspiro[4,5]decan-4-one privileged structure that engenders PLD2 selectivity.

Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part II. Identification of the 1,3,8-triazaspiro[4,5]decan-4-one privileged structure that engenders PLD2 selectivity.

Bioorganic & medicinal chemistry letters (2009-03-21)
Robert Lavieri, Sarah A Scott, Jana A Lewis, Paige E Selvy, Michelle D Armstrong, H Alex Brown, Craig W Lindsley
ABSTRACT

This Letter describes the synthesis and structure-activity relationships (SAR) of isoform-selective PLD inhibitors. By virtue of the installation of a 1,3,8-triazaspiro[4,5]decan-4-one privileged structure, PLD inhibitors with nanomolar potency and an unprecedented 40-fold selectivity for PLD2 over PLD1 were developed. Interestingly, SAR for this diverged from our earlier efforts, and dual PLD1/2 inhibitors were also discovered within this series.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-(2-Pyridyl)piperazine, ≥99%
Avanti
VU0285655-1, N-{2-[4-oxo-1-phenyl-1,3,8-triazaspiro(4.5)decan-8-yl]ethyl}quinoline-3-carboxamide, powder