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  • Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part I: Impact of alternative halogenated privileged structures for PLD1 specificity.

Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part I: Impact of alternative halogenated privileged structures for PLD1 specificity.

Bioorganic & medicinal chemistry letters (2009-03-10)
Jana A Lewis, Sarah A Scott, Robert Lavieri, Jason R Buck, Paige E Selvy, Sydney L Stoops, 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 alternative halogenated piperidinyl benzimidazolone privileged structures, in combination with a key (S)-methyl group, novel PLD inhibitors with low nM potency and unprecedented levels of PLD1 isoform selectivity (approximately 1700-fold) over PLD2 were developed.

MATERIALS
Product Number
Brand
Product Description

Avanti
VU0359595, (1R,2R)-N-([S]-1-{4-[5-bromo-2-oxo-2,3-dihydro-1H-benzo(d)imidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxamide, powder
Sigma-Aldrich
4-(2-Keto-1-benzimidazolinyl)piperidine, 98%