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Synthesis of [(3) H] and [(2) H6 ]AZD6642, an inhibitor of 5-lipoxygenase activating protein (FLAP).
- Source :
-
Journal of labelled compounds & radiopharmaceuticals [J Labelled Comp Radiopharm] 2016 Jul; Vol. 59 (9), pp. 340-5. Date of Electronic Publication: 2016 Jun 14. - Publication Year :
- 2016
-
Abstract
- An AstraZeneca effort to identify a 5-lipoxygenase activating protein inhibitor with good drug-like properties resulted in the identification of AZD6642. To further understand its drug metabolism and pharmacokinetic properties, it was required labeled with tritium. The tritiation of AZD6642 was effected by Ir-catalyzed exchange chemistry to give an average of one tritium per molecule. Additionally, a stable isotope labeled version of AZD6642 was required to support bioanalytical studies. The synthesis originated from [(2) H6 ]acetone which was converted to the trimethylsilyl cyanide adduct and subsequently reduced to give 2-(aminomethyl)-[1,1,1,3,3,3-(2) H6 ]propan-2-ol in good yield. Carbonylation to give an amide adduct resulted in an intermediate that was converted to the final compound in four steps.<br /> (Copyright © 2016 John Wiley & Sons, Ltd.)
- Subjects :
- 5-Lipoxygenase-Activating Protein Inhibitors chemistry
5-Lipoxygenase-Activating Protein Inhibitors pharmacology
Acetone chemistry
Chemistry Techniques, Synthetic
Isotope Labeling
Picolinic Acids chemistry
Picolinic Acids pharmacology
Pyrazines chemistry
Pyrazines pharmacology
5-Lipoxygenase-Activating Protein Inhibitors chemical synthesis
5-Lipoxygenase-Activating Proteins metabolism
Picolinic Acids chemical synthesis
Pyrazines chemical synthesis
Tritium chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1099-1344
- Volume :
- 59
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Journal of labelled compounds & radiopharmaceuticals
- Publication Type :
- Academic Journal
- Accession number :
- 27298225
- Full Text :
- https://doi.org/10.1002/jlcr.3409