Base-catalyzed deuterium and tritium labeling of aryl methyl sulfones

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 47, Issue 12, 2004, Pages 881-889

  Scheigetz, John ^a   Berthelette, Carl ^a   Li, Chun ^a   Zamboni, Robert J ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

Cyclooxygenase 2; DP receptor antagonists; Labeled compounds; Methyl sulfone exchange; Tritium

Indexed keywords

CATALYSIS; DEUTERIUM; MASS SPECTROMETRY;

BASE CATALYZED; CYCLOOXYGENASE 2; DP RECEPTOR ANTAGONIST; EXCHANGE REACTION; LABELED COMPOUND; LABELINGS; METHYL SULPHONE EXCHANGE; POTENT INHIBITOR; RECEPTOR ANTAGONISTS; SELECTIVE INHIBITORS;

TRITIUM;

AROMATIC HYDROCARBON; BASE; CYCLOOXYGENASE 2 INHIBITOR; DEUTERIUM; DIMETHYL SULFONE; PROSTAGLANDIN D2; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; RADIOPHARMACEUTICAL AGENT; TRITIUM;

ARTICLE; BASE PAIRING; CATALYST; COMPARATIVE STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ISOTOPE LABELING; MASS SPECTROMETRY; NUCLEIC ACID BASE SUBSTITUTION; RADIOACTIVITY; STRUCTURE ANALYSIS;

TRITIUM;

EID: 8844234941     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlcr.880     Document Type: Article

References (17)

1. Roy P, Leblanc Y, Ball RG, Brideau C, Chan CC, Chauret N, Cromlish W, Ethier D, Gauthier JY, Gordon R, Greig G, Guay J, Kargman S, Lau CK, O'Neill G, Silva J, Thérien M, Van Staden C, Wong E, Xu L, Prasit P. Bioorg Med Chem Lett 1997; 7: 57.
2. Thérien M, Brideau C, Chan CC, Cromlish W, Gauthier JY, Gordon R, Greig G, Kargman S, Lau CK, Leblanc Y, Li CS, O'Neill G, Riendeau D, Roy P, Wang Z, Xu L, Prasit P. Bioorg Med Chem Lett 1997; 7: 47.
3. Chauret N, Nicoll-Griffith D. Drug Metab Dispos 1995; 23: 1325.
4. (a) Labelle M, Sturino C, Roy B. Prostaglandin D2 receptor antagonists. PCT Int. Appl. WO01/79169 A2, 2001.
5. (b) Labelle M, Sturino C, Roy B, Berthelette C, Boyd M, Lachance N, Scheigetz J. Cyclopentanoindole, compositions containing such compounds and methods of treatment. PCT Int. Appl. US 6,410,583 B1, 2002.
6. (c) Berthelette C, Lachance N, Li L, Sturino C, Wang Z. Fluoro substituted cycloalkanoindoles, compositions containing such compounds and methods of treatment. PCT Int. Appl. US 2003/0158246 A1, 2003.
7. Leblanc Y, Gauthier JY, Ethier D, Guay J, Mancini J, Riendeau D, Tagari P, Vickers P, Wong E, Prasit P. Bioorg Med Chem Lett 1995; 5: 2123.
8. (a) Broaddus CD. J Amer Chem Soc 1968; 90: 5504.
9. (b) Tupitsyn IF, Zatsepina NN. Zh Obshch Khim 1982; 52: 994.
10. (c) Ponsart S, Coudane J, Morgat J-L, Vert M. J Label Compd Radiopharm 2000; 43: 271.
11. (d) Brown MD, Cook MJ, Hutchinson BJ, Katritzky AR. Tetrahedron 1971; 27: 593.
12. (e) MacCulloch AC, Walker RT. Tetrahedron 1998; 54: 12457.
13. (a) Belley M, Leblanc Y, Gauthier JY, Li CS, Grimm E, Thérien M, Black C, Prasit P, Lau CK, Roy P. PCT Int. Appl. W097/14691, 1997 (Compounds 2-5).
14. (b) Dubé D, Fortin R, Friesen R, Gauthier JY, Wang Z. PCT Int. Appl. W098/03484, 1998 (Compound 6).
15. (c) Black C, Léger S, Prasit P, Wang Z, Hughes G, Han Y, Hamel P. PCT Int. Appl. W097/16435, 1997 (Compound 7).
16. Chauret N, Guay D, Li C, Day S, Silva J, Blouin M, Ducharme Y, Yergey JA, Nicoll-Griffith DA. Bioorg Med Chem Lett 2002; 12: 2149.
17. Nicoll-Griffith DA, Chauret N, Yergey JA, Trimble LA, Favreau L, Zamboni R, Grossman SJ, Drey J, Herold E. Drug Metab Dispos 1993; 21: 861.