Synthesis and deuterium labelling of the pure selective estrogen receptor modulator (SERM) acolbifene glucuronides

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 50, Issue 3, 2007, Pages 197-206

  Sancéau, Jean Yves ^a   Larouche, Denis ^a   Caron, Brigitte ^a   Bélanger, Patrick ^a   Coquet, Agnès ^a   Bélanger, Alain ^a   Labrie, Fernand ^a   Gauthier, Sylvain ^a  

^a LAVAL UNIVERSITY   (Canada)

Author keywords

Acolbifene (EM 652 HCl); Acolbifene glucuronides; Deuterium; Metabolites; SERM

Indexed keywords

MAGNESIUM COMPOUNDS; METABOLITES;

ACOLBIFENE (EM-652·HCL); ACOLBIFENE GLUCURONIDE; BREAST CANCER; CLINICAL DEVELOPMENT; DEUTERIUM LABELLING; GLUCURONIDES; LATE STAGE; OESTROGENS; ORALLY ACTIVE; SELECTIVE ESTROGEN RECEPTOR MODULATORS;

DEUTERIUM;

4 CHROMANONE DERIVATIVE; 7 (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID) 3 (4' HYDROXYPHENYL) 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1` BENZOPYRAN; 7 (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID) 3 (4' TERT BUTYLDIMETHYLSILYLOXYPHENYL) 4 METHYL 2 [4'' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID) 3 [4' (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID)PHENYL] 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN 2 H3; 7 (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID) 3 [4' (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE)PHENYL] 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE) 3 (4' HYDROXYPHENYL) 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE) 3 (4' TERT BUTYLDIMETHYLSILYLOXYPHENYL) 4 METHYL 2 [4'' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE) 3 [4' (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE)PHENYL] 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 HYDROXY 3 (4' HYDROXYPHENYL) 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1` BENZOPYRAN 10 CAMPHORSULFONIC ACID SALT 2 H3 2 H3; 7 HYDROXY 3 (4' HYDROXYPHENYL) 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1` BENZOPYRAN ACOLBIFENE 2 H3 2 H3; 7 HYDROXY 3 (4' TERT BUTYLDIMETHYLSILYLOXYPHENYL) 4 METHYL 2 [4' [2' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 HYDROXY 3 [4' (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID)PHENYL] 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN 2 H3; 7 HYDROXY 3 [4' (BETA DEXTRO GLUCOPYRANOSYLURONIC ACID)PHENYL] 4 METHYL 2 [4'[2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 HYDROXY 3 [4' (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE)PHENYL] 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 TERT BUTYLDIMETHYLSILYLOXY 3 (4' HYDROXYPHENYL) 4 METHYL 2 [4' [2'' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; 7 TERT BUTYLDIMETHYLSILYLOXY 3 [4' (METHYL 2,3,4 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYLURONATE) HYDROXYPHENYL)PHENYL] 4 METHYL 2 [4' [2' (1 PIPERIDINO)ETHOXY]PHENYL] 2H 1 BENZOPYRAN; ACOLBIFENE 4' GLUCURONIDE; ACOLBIFENE 7 GLUCURONIDE; ACOLBIFENE GLUCURONIDE; DEUTERIUM; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

EID: 34248563377     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1260     Document Type: Article

References (21)

1. Labrie F, Champagne P, Labrie C, Roy J, Laverdière J, Provencher L, Potvin M, Drolet Y, Pollak M, Panasci L, L'Espérance B, Dufresne J, Latreille J, Robert J, Samson B, Jolivet J, Yelle L, Cusan L, Diamond P, Candas B. J Clin Oncol 2004; 22: 864-871.
2. Labrie F, Labrie C, Bélanger A, Simard J, Giguère V, Tremblay A, Tremblay G. J Steroid Biochem Mol Biol 2002; 79: 213-225.
3. Labrie F, Labrie C, Bélanger A, Giguère V, Simard J, Mérand Y, Gauthier S, Luu-The V, Candas B, Martel C, Luo S. Adv Protein Chem 2001; 56: 293-368.
4. Labrie F, Labrie C, Bélanger A, Simard J, Gauthier S, Luu-The V, Mérand Y, Giguère V, Candas B, Luo S, Martel C, Singh SM, Fournier M, Coquet A, Richard V, Charbonneau R, Charpenet G, Tremblay A, Tremblay G, Cusan L, Veilleux R. J Steroid Biochem Mol Biol 1999; 69: 51-84.
5. Sancéau JY, Labrie F, Gauthier S. J Label Compd Radiopharm 2004; 47: 741-752.
6. High K, Baker SJ, Bélanger A, Labrie C, Labrie F. Proceedings of the 9th North American ISSX Meeting 1999, vol. 15. International Society for the Study of Xenobiotics: Nashville, TN, 1999; 76.
7. Barbier O, Albert C, Martineau I, Vallée M, High K, Labrie F, Hum DW, Labrie C, Bélanger A. Mol Pharmacol 2001; 59: 636-645.
8. Sancéau JY, Larouche D, Caron B, Bélanger P, Coquet A, Bélanger A, Gauthier S, Labrie F. 230th ACS National Meeting, Washington, August 2005, MEDI-028.
9. Stachulski AV, Jenkins GN. Nat Prod Rep 1998; 15: 173-186.
10. Melvin F, McNeill A, Henderson PJF, Herbert RB. Tetrahedron Lett 1999; 40: 1201-1202.
11. Briggs BS, Baker PJ, Belvo MD, Black TD, Getman BG, Kemp CAJ, Muth WL, Perun TJ, Strobel Jr RJ, Paschal JW, Zmijewski MJ. J Ind Microbiol Biotechnol 1999; 23: 194-197.
12. (a) Berrang BD, Wyrick CD, Carroll FI, Seltzman HH. J Label Compd Radiopharm 1999; 42: 851-857;
13. (b) Conrow RB, Bernstein S. J Org Chem 1971, 36: 863-870.
14. McCague R, Parr IB, Leclercq G, Leung OT, Jarman M. Biochem Pharmacol 1990; 39: 1459-1465.
15. (a) Dodge JA, Lugar CW, Cho S, Osborn JJ, Phillips DL, Glasebrook AL, Frolik CA. Bioorg Med Chem Lett 1997; 7: 993-996;
16. (b) Dodge JA, Lugar CW, Cho S, Short LL, Sato M, Yang NN, Spangle LA, Martin MJ, Phillips DL, Glasebrook AL, Osborn JJ, Frolik CA, Bryant HU. J Steroid Biochem Mol Biol 1997; 61: 97-106.
17. Schmidt RR. Pure Appl Chem 1989; 61: 1257-1270.
18. Miller CP, Collini MD, Tran BD, Chan AWY, Rubezhov AZ. WO0119839 A1 American Home Products Corporation (March 2001). 17. Brown RT, Scheinmann F, Stachulski AV. J Chem Res (S) 1997; 10: 370-371.
19. Rasku S, Wähälä K, Koskimies J, Hase T. Tetrahedron 1999; 55: 3445-3454.
20. Gauthier S, Caron B, Cloutier J, Dory YL, Favre A, Larouche D, Mailhot J, Ouellet C, Schwerdtfeger A, Leblanc G, Martel C, Simard J, Mérand Y, Bélanger A, Labrie C and Labrie F. J Med Chem 1997; 40: 2117-2122.
21. Draper RW, Iyer RV, Lu Y, Vater EJ. US6262270 B1 Schering Corporation (July 2001); Draper RW, Iyer RV, Lu Y, Vater EJ. WO0009493 A1 Schering Corporation (February 2000).