A novel five‐lipoxygenase activity protein inhibitor labeled with carbon‐14 and deuterium. (20th July 2015)

• Record Type: Journal Article
• Authors: Latli, Bachir; Hrapchak, Matt; Gao, Joe J.; Busacca, Carl A.; Senanayake, Chris H.
• Is Part Of: Journal of labelled compounds & radiopharmaceuticals. Volume 58:Number 9(2015)
• Page Start: 390
• Page End: 394
• Publication Date: 2015-07-20
• Subjects: Tracers (Chemistry) -- Periodicals; Radiopharmaceuticals -- Periodicals; 615.8424
• DOI: 10.1002/jlcr.3319
• Languages: English
• ISSNs: 0362-4803

Abstract

<abstract abstract-type="main" id="jlcr3319-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p id="jlcr3319-para-0001">2‐[4‐(3‐{(1<italic>R</italic>)‐1‐[4‐(2‐Aminopyrimidin‐5‐yl)phenyl]‐1‐cyclopropylethyl}‐1, 2, 4‐oxadiazol‐5‐yl)‐1<italic>H</italic>‐pyrazol‐1‐yl]‐<italic>N</italic>, <italic>N</italic>‐dimethylacetamide (1), is a novel and selective five‐lipoxygenase activity protein (FLAP) inhibitor with excellent pharmacokinetics properties. The availability of a key chiral intermediate allowed the synthesis of [¹⁴C]‐(1) in six radiochemical steps and in 47% overall radiochemical yield with a specific activity of 51 mCi/mmol using carbon‐14 zinc cyanide. 2‐Chloro‐<italic>N</italic>, <italic>N</italic>‐dimethyl‐²H₆‐acetamide was prepared and condensed with a penultimate intermediate to give [²H₆]‐(1) in very high yield and in more than 99% isotopic enrichment.</p> </abstract>