Design, synthesis, radiolabeling, and in vitro and in vivo evaluation of bridgehead iodinated analogues of N -{2-[4-(2-methoxyphenyl)piperazin-1-yl] ethyl}- N -(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) as potential SPECT ligands for the 5-HT1A receptor

Journal of Medicinal Chemistry

Volumn 54, Issue 10, 2011, Pages 3480-3491

  Al Hussainy, Rana ^a   Verbeek, Joost ^a   Van Der Born, Dion ^a   Braker, Anton H ^a   Leysen, Josée E ^a   Knol, Remco J ^b   Booij, Jan ^b   Herscheid, D M ^a  

^a VU UNIVERSITY MEDICAL CENTER   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

4 IODO N [2 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]ETHYL] N (PYRIDIN 2 YL)CUBYL 1 CARBOXAMIDE I 123; BICYCLO COMPOUND; CARBON; IODINE 123; IODINE DERIVATIVE; N [2 [4 (2 HYDROXYPHENYL)PIPERAZIN 1 YL]ETHYL] 4 IODO N (PYRIDIN 2 YL)CUBYL 1 CARBOXAMIDE I 123; N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; SEROTONIN 1A RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TISSUE LEVEL; HUMAN; HUMAN TISSUE; IN VITRO STUDY; IN VIVO STUDY; IODINATION; ISOTOPE LABELING; NONHUMAN; RAT; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HEPATOCYTES; HUMANS; IODINE; KINETICS; LIGANDS; MODELS, CHEMICAL; PIPERAZINES; PYRIDINES; RATS; RECEPTOR, SEROTONIN, 5-HT1A; SOLVENTS; TIME FACTORS; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 79957759309     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1009956     Document Type: Article

References (52)

1. 1A receptors: considerations on receptor effector coupling across systems Neuropharmacology 1997, 36, 429-437 (Pubitemid 27272087)
2. Frazer, A.; Maayani, S.; Wolfe, B. B. Subtypes of receptors for serotonin Annu. Rev. Pharmacol. Toxicol. 1990, 30, 307-348
3. Passchier, J.; Van Waarde, A. Visualisation of serotonin-1A (5-HT1A) receptors in the central nervous system Eur. J. Nucl. Med. 2001, 28, 113-129 (Pubitemid 32120814)
4. Saxena, P. R. Serotonin receptors: subtypes, functional responses and therapeutic relevance Pharmacol. Ther. 1995, 66, 339-368
5. 1A receptors Nucl. Med. Biol. 2000, 27, 437-439
6. 1A binding-sites in frontal cortex of suicide victims J. Neural Transm. 1991, 85, 181-194
7. Drevets, W. C.; Frank, E.; Price, C. J.; Kupfer, D. J.; Holt, D.; Greer, P. J.; Huang, Y.; Gautier, C.; Mathis, C. PET imaging of serotonin 1A receptor binding in depression Biol. Psychiatry 1999, 46, 1375-1387
8. cBlane, J. W. 5-HT drugs in animal models of anxiety Psychopharmacology 1993, 112, 13-20 (Pubitemid 23261851)
9. Kepe, V.; Barrio, J. R.; Cheng Huang, S.; Ercoli, L.; Siddarth, P.; Shoghi Jadid, K.; Cole, G. M.; Satyamurthy, N.; Cummings, J. L.; Small, G. W.; Phelps, M. E. Serotonin 1A receptors in the living brain of Alzheimer's disease patients Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 702-707 (Pubitemid 43153089)
10. 1A receptors in vivo Prog. Med. Chem. 2001, 38, 189-247
11. 1A receptor in schizophrenia: a promising target for novel atypical neuroleptics? Psychopharmacology 2001, 15, 37-46 (Pubitemid 32242102)
12. 1A receptors J. Pharmacol. Exp. Ther. 2000, 295, 853-861
13. 1A receptor binding in amygdala of schizophrenia Biol. Psychiatry 2004, 55, 439-444 (Pubitemid 38338529)
14. 1A receptor antagonist Br. J. Pharmacol. 1994, 112, 91P
15. 1A receptor PET radioligands Nucl. Med. Biol. 2000, 27, 441-447 (Pubitemid 30658144)
16. 11C]-WAY 100635 Med. Chem. Res. 1994, 5, 208-227
17. Pike, V. W.; Halldin, C.; Wikström, H.; Marchais, S.; McCarron, J. A.; Sandell, J.; Nowicki, B.; Swahn, C-G; Osman, S.; Hume, S. P.; Constantinou, M.; Andree, B.; Farde, L. Radioligands for the study of brain 5-HT1A receptors in vivo-development of some new analogues of WAY Nucl. Med. Biol. 2000, 27, 449-455 (Pubitemid 30658145)
18. 1A ligand J. Med. Chem. 1994, 37, 1406-1407 (Pubitemid 24174075)
19. 1A receptors in rat brain Synapse 1994, 18, 359-366 (Pubitemid 24357836)
20. 123I] p -MPPI in nonhuman primates Synapse 1996, 24, 273-281 (Pubitemid 26386839)
21. Cliffe, I. A.; Mansell, H. L. European Patent 0 512 755 A2, 1993.
22. Lednicer, D.; Grostic, M. F. Selective demethylation of deoxyanisoin. Mass spectra of the products J. Org. Chem. 1967, 32, 3251-3253
23. Stone, H.; Shechter, H. 1,6-Diiodohexane. Organic Syntheses; Wiley & Sons: New York, 1963; Collect. Vol. 4, p 323
24. Org. Synth. 1951, 31, 31.
25. Stetter, H.; Mayer, J. Hersellung und eigenschaften von in 3-stellung substituierten adamantan-carbonsäuren-(1) Chem. Ber. 1962, 95, 667-672
26. Eaton, P. E.; Nordari, N.; Tsanaktsidis, J.; Upadhyaya, S. P. Barton decarboxylation of cubane-1,4-dicarboxylic acid: optimized procedures for cubanecarboxylic acid and cubane Synthesis 1995, 501-502
27. Harpp, D. N.; Priefer, R.; Farrell, P. G. Effective synthetic routes to cubylcarbinol analogues Synthesis 2002, 2671-2673 (Pubitemid 36034424)
28. Moriarty, R. M.; Khosrowshahi, J. S.; Daleck, T. M. Hypervalent iodine iodinative decarboxylation of cubyl and homocubyl carboxylic acids J. Chem. Soc., Chem. Commun. 1987, 675-676
29. Humber, L. G.; Myers, G.; Hawkins, L.; Schmidt, C.; Boulerice, M. Agents affecting lipid metabolism XIII. The synthesis of 1,4-disubstituted bicyclo[2.2.2]octane analogues Can. J. Chem. 1964, 42, 2852-2860
30. Roberts, J. D.; Moreland, W. T.; Frazer, W. Synthesis of some 4-substituted bicyclo[2.2.2]octane-1-carboxylic acids J. Am. Chem. Soc. 1953, 75, 637-640
31. Mozingo, R.; Adkins, H.; Richards, L. Catalyst, Raney Nickel, W-2. Organic Syntheses; Wiley & Sons: New York, 1955; Collect. Vol. 3, p 181
32. Org. Synth. 1941, 21, 15.
33. Sukenik, C. N.; Wang, S. S.; Kumar, K. Synthesis, characterization, and chemistry of bridgehead-functionalized bicyclo[2.2.2]octanes: reactions at neopentyl sites J. Org. Chem. 1984, 49, 665-670
34. Della, E. W.; Tsanaktsidis, J. Synthesis of bridgehead-bridgehead substituted bicycloalkanes Aust. J. Chem. 1985, 38, 1705-1718
35. Vögtle, N. G.; Danielmeier, K.; Steckhan, E. Rodlike molecules by Kolbe electrolysis Synthesis 1996, 71-75
36. Bunce, N. J. A mercury salt pathway for the degradation of carboxylic acids to alkyl halides using halogen and mercuric oxide J. Org. Chem. 1974, 37, 664-669
37. Ben, R. N.; Breau, L.; Bensimon, C.; Durst, T. Unusual stereochemical results in the reaction of alpha-lithio analogues of bicyclic sulfoxides Tetrahedron. 1994, 50, 6061-6076 (Pubitemid 24152276)
38. 4 of oleic acid, other monoenic fatty acids and alkenes Tetrahedron Lett. 2005, 46, 3201-3203
39. Ottenheijm, H. C. J.; Tijhuis, W. M. Acid Chlorides from α-Keto Acids with α,α-Dichloromethyl Methyl Ether: Pyruvoyl Chloride. Organic Syntheses; Wiley & Sons: New York, 1990; Collect. Vol. 7, p 467
40. Org. Synth. 1983, 61, 1.
41. Braker, A. H.; Moet, F. P.; van der Zwart, R. E.; Eersels, J. L. H.; Herscheid, J. D. M. Adsorption of radioiodine on platinum: a fast simple column method to obtain concentrated and pure radioiodide in either water or anhydrous solvents Appl. Radiat. Isot. 2002, 57, 475-482
42. 50) of an enzymatic reaction Biochem. Pharmacol. 1973, 22, 3099-3108
43. 4 receptor agonist Psychopharmacology 2006, 188, 244-251 (Pubitemid 44371162)
44. 18F]MPPF, a fluoro analog of WAY-100635 Nucl. Med. Biol. 1998, 25, 343-350 (Pubitemid 28219097)
45. 11C]WAY-100635, in monkey and human plasma by HPLC: comparison of the behaviour of an identified radioactive metabolite with parent radioligand in monkey using PET Nucl. Med. Biol. 1996, 23, 627-634 (Pubitemid 26295578)
46. Damhaut, P.; Plenevaux, A.; Lemaire, C.; Aerts, J.; Biver, F.; Monclus, M.; Luxen, A.; Goldman, S. In vivo studies of [18F] p -MPPF metabolites in human J. Labelled Compd. Radiopharm. 1999, 42 (suppl 1) S661-S662
47. Eaton, P. E. Cubanes: starting materials for the chemistry of the 1990s and the new century Angew. Chem., Int. Ed. Engl. 1992, 31, 1421-1436
48. 1A receptors: syntheses, radiosyntheses, and in vitro and in vivo evaluation Nucl. Med. Biol. 1998, 25, 769-776 (Pubitemid 28557103)
49. Waterhouse, R. N. Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents Mol. Imaging. Biol. 2003, 5, 376-389 (Pubitemid 37489828)
50. Maksić, Z. B.; Eckert- Maksić, M.; Randić, M. Correlation between C-H and C-C spin-spin coupling constants and s character of hyprids calculated by the maximum overlap method Theor. Chim. Acta 1971, 22, 70-79
51. Randić, M.; Stefanović, D. Hybridisation in norbornane and some analogues by the method of maximum overlap J. Chem. Soc.B 1968, 423-425
52. 1A receptors with positron emission tomography Life Sci. 1994, 55, 403-407