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Current Radiopharmaceuticals


ISSN (Print): 1874-4710
ISSN (Online): 1874-4729

Synthesis of a Potent Cathepsin S Inhibitor Labeled with Deuterium and Carbon-14

Author(s): Bachir Latli, Matt Hrapchak, Jon C. Lorenz, Carl A. Busacca and Chris Senanayake

Volume 5, Issue 4, 2012

Page: [314 - 317] Pages: 4

DOI: 10.2174/1874471011205040314

Price: $65


Morpholine-4-carboxylic acid {(S)-1-[4-cyano-1-(3-morpholin-4-yl-propyl)-piperidin-4-ylcarbamoyl]-4,4- dimethyl-hexyl}-amide, (1) is a potent reversible and selective cathepsin S inhibitor. Deuterium labeled (1) was prepared in four steps in 62% overall yield from [2H8]- morpholine and chiral acid (6). Carbon-14 labeled (1) was obtained in two steps using sodium [14C]-cyanide in a modified Strecker reaction followed by amide bond formation with acid (6) in 74% overall radiochemical yield. The phosphate salt of this compound was produced by treatment with phosphoric acid in methanol in 97% yield.

Keywords: Cathepsin S, carbon-14, deuterium, radiosynthesis.

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