Synthesis and structure-affinity relationships of new 4-(6-iodo-H- imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine derivatives as ligands for human β-amyloid plaques

Journal of Medicinal Chemistry

Volumn 50, Issue 19, 2007, Pages 4746-4758

  Cai, Lisheng ^a   Cuevas, Jessica ^a   Temme, Sebastian ^a   Herman, Mary M ^a   Dagostin, Claudio ^b   Widdowson, David A ^b   Innis, Robert B ^a   Pike, Victor W ^a  

^a NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 1H IMIDAZO[1,2 B]PYRAZOLE; 4 (6 IODO H IMIDAZO[1,2 A]PYRIDIN 2 YL) N DIMETHYLBENZENEAMINE DERIVATIVE; AMYLOID BETA PROTEIN; RADIOLIGAND; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; BINDING AFFINITY; DRUG BINDING SITE; DRUG SYNTHESIS; LIPOPHILICITY; POSITRON EMISSION TOMOGRAPHY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ACTIVITY RELATION;

AGED, 80 AND OVER; ALZHEIMER DISEASE; AMYLOID BETA-PROTEIN; ANILINE COMPOUNDS; BRAIN; FEMALE; HUMANS; IMIDAZOLES; IODINE; LIGANDS; PEPTIDE FRAGMENTS; PROTEIN BINDING; PYRIDINES; RADIOLIGAND ASSAY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34648822430     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0702231     Document Type: Article

References (51)

1. Selkoe, D. J. Alzheimer's disease: genes, proteins, and therapy. Physiol. Rev. 2001, 81, 741-766.
2. Hardy, J. A.; Higgins, G. A. Alzheimer's disease: the amyloid cascade hypothesis. Science 1992, 256, 184-185.
3. Klunk, W. E.; Engler, H.; Nordberg, A.; Wang, Y.; Blomqvist, G.; Holt, D. P.; Bergstrom, M.; Savitcheva, I.; Huang, G. F.; Estrada, S.; Ausen, B.; Debnath, M. L.; Barletta, J.; Price, J. C.; Sandell, J.; Lopresti, B. J.; Wall, A.; Koivisto, P.; Antoni, G.; Mathis, C. A.; Langstrom, B. Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. Ann. Neurol. 2004, 55, 306-319.
4. Shoghi-Jadid, K.; Small, G. W.; Agdeppa, E. D.; Kepe, V.; Ercoli, L. M.; Siddarth, P.; Read, S.; Satyamurthy, N.; Petric, A.; Huang, S. C.; Barrio, J. R. Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease. Am. J. Geriatr. Psychiatry 2002, 10, 24-35.
5. Verhoeff, N. P.; Wilson, A. A.; Takeshita, S.; Trop, L.; Hussey, D.; Singh, K.; Kung, H. F.; Kung, M. P.; Houle, S. In-vivo imaging of Alzheimer disease beta-amyloid with [11C]SB-13 PET. Am. J. Geriatr. Psychiatry 2004, 12, 584-595.
6. Newberg, A. B.; Wintering, N. A.; Plossl, K.; Hochold, J.; Stabin, M. G.; Watson, M.; Skovronsky, D.; Clark, C. M.; Kung, M. P.; Kung, H. F. Safety, biodistribution, and dosimetry of 123I-IMPY: a novel amyloid plaque-imaging agent for the diagnosis of Alzheimer's disease. J. Nucl. Med. 2006, 47, 748-754.
7. Klunk, W. E.; Lopresti, B. J.; Debnath, M. L.; Holt, D. P.; Wang, Y.; Huang, G.-F.; Shao, L.; Lefterov, I.; Koldamova, R.; Ikonomovic, M.; DeKosky, S. T.; Mathis, C. A. Amyloid deposits in transgenic PS1/APP mice do not bind the amyloid PET tracer, PIB, in the same manner as human brain amyloid. Neurobiol. Aging 2004, 25, 232-233.
8. Mathis, C. A.; Wang, Y.; Klunk, W. E. Imaging beta-amyloid plaques and neurofibrillary tangles in the aging human brain. Curr. Pharm. Des. 2004, 10, 1469-1492.
9. Dishino, D. D.; Welch, M. J.; Kilbourn, M. R.; Raichle, M. E. Relationship between lipophilicity and brain extraction of C-11-labeled radiopharmaceuticals. J. Nucl. Med. 1983, 24, 1030-1038.
10. Pike, V. W. Positron-emitting radioligands for studies in vivo. Probes for human psychopharmacology. J. Psychopharmacol. 1993, 7, 139-158.
11. 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.
12. Kung, M. P.; Hou, C.; Zhuang, Z. P.; Zhang, B.; Skovronsky, D.; Trojanowski, J. Q.; Lee, V. M.; Kung, H. F. IMPY: an improved thioflavin-T derivative for in vivo labeling of beta-amyloid plaques. Brain Res. 2002, 956, 202-210.
13. Kung, M. P.; Zhuang, Z. P.; Hou, C.; Jin, L. W.; Kung, H. F. Characterization of radioiodinated ligand binding to amyloid beta plaques. J. Mol. Neurosci. 2003, 20, 249-254.
14. 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J. Med. Chem. 2003, 46, 2740-2754.
15. Zhuang, Z. P.; Kung, M. P.; Wilson, A.; Lee, C. W.; Plossl, K.; Hou, C.; Holtzman, D. M.; Kung, H. F. Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting beta-amyloid plaques in the brain. J. Med. Chem. 2003, 46, 237-243.
16. 18F-labeled imidazo[1,2-a]pyridine analogues as potential agents for imaging beta-amyloid in Alzheimer's disease. Bioorg. Med. Chem. Lett. 2006, 16, 3015-3018.
17. Cai, L.; Innis, R. B.; Pike, V. W. Radioligand development for PET imaging of beta-amyloid-current status. Curr. Med. Chem. 2007, 14, 19-52.
18. 18F-labeled 6-iodo-2-(4′-N,N-dimethylamino)phenylimidazo[1,2-a]pyridine derivatives as prospective radioligands for beta-amyloid in Alzheimer's disease. J. Med. Chem. 2004, 47, 2208-2218.
19. Hu, J.; Li, Z.; Li, Y.; Tang, L.; Wu, M. Method of Synthesizing 5-[1-Hydroxy-2-(isopropylamino)ethyl]aminobenzonitrile. CN95-103024-19950403, CN1120535A19960417, 1996.
20. Cai, L.; Brouwer, C.; Sinclair, K.; Cuevas, J.; Pike, V. W. Titanium-(IV) chloride-promoted synthesis of new imidazo[1,2a]pyridine derivatives under microwave conditions. Synthesis 2006, 133-145.
21. Hu, Z. Process for Synthesizing Ketoprofen. CN 95 109877 19950824, CN 1143624 A1 9970226, 1997.
22. Kuhla, D. E.; Campbell, H. F.; Studt, W. L.; Molino, B. F. Bicyclic heteroaryl thiazole compounds and their cardiotonic uses. WO 85 US2522 19851218, WO 8603749 A1 19860703, 1986.
23. Otsuka Pharmaceutical Co., Ltd. Carbostyril Derivatives and a Cardiotonic Composition Containing Them. BE 82 207321 19820215, BE 892148 A1 19820816, 1982.
24. Van de Poel, H.; Guillaumet, G.; Viaud-Massuard, M. C. Synthesis of melatonin analogues derived from furo[2,3-b]- and [2,3-c]pyridines by use of a palladium-copper catalyst system. Heterocycles 2002, 57, 55-71.
25. Capdevielle, P.; Maumy, M. Esters are effective cocatalysts in copper-catalyzed methanolysis of aryl bromides. Tetrahedron Lett. 1993, 34, 1007-1010.
26. Sundberg, R. J.; Dahlhausen, D. J.; Manikumar, G.; Mavunkel, B.; Biswas, A.; Srinivasan, V.; King, F., Jr.; Waid, P. Preparation of 2-aryl- and 2-(aryloxymethyl)imidazo[1,2-a]pyridines and related compounds. J. Heterocycl. Chem. 1988, 25, 129-137.
27. Gol'dfarb, Y.; Stoyanovich, F. M.; Marakatkina, M. A.; Gorushkina, G. 1. Synthesis of 6-(alkylthio)imidazo[1,2-a]pyridines. Khim. Geterotsikl. Soedin. 1979, 634-638.
28. Bochis, R. J.; Olen, L. E.; Waksmunski, F. S.; Mrozik, H.; Eskola, P.; Kulsa, P.; Wilks, G.; Taylor, J. E.; Egerton, J. R.; Ostlind, D. A.; Olson, G. Substituted imidazo[1,2-a]pyridine-2-carbamate anthelmintics. J. Med. Chem. 1981, 24, 1518-1521.
29. Enguehard, C.; Allouchi, H.; Gueiffier, A.; Buchwald, S. L. Easy access to novel substituted 6-aminoimidazo[1,2-a]pyridines using palladium- and copper-catalyzed aminations. J. Org. Chem. 2003, 68, 4367-4370.
30. Barlin, G. B.; Davies, L. P.; Ireland, S. J.; Ngu, M. M. L.; Zhang, J. K. Imidazo[1,2-B]pyridazines. 12. Syntheses and central-nervous-system activities of some substituted imidazo[1,2-B]pyridazines and related imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyrazines. Aust. J. Chem. 1992, 45, 877-888.
31. Vickery, E. H.; Pahler, L. F.; Eisenbraun, E. J. Selective O-demethylation of catechol ethers-Comparison of boron tribromide and iodotrimethylsilane. J. Org. Chem. 1979, 44, 4444-4446.
32. Cai, L.; Cuevas, J.; Peng, Y. Y.; Pike, V. W. Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions. Tetrahedron Lett. 2006, 47, 4449-4452.
33. Klunk, W. E.; Wang, Y.; Huang, G. F.; Debnath, M. L.; Holt, D. P.; Shao, L.; Hamilton, R. L.; Ikonomovic, M. D.; DeKosky, S. T.; Mathis, C. A. The binding of 2-(4′-methylaminophenyl)benzothiazole to postmortem brain homogenates is dominated by the amyloid component. J. Neurosci. 2003, 23, 2086-2092.
34. Eriksson, J.; Ulin, J.; Langstrom, B. [C-1]methyl iodide from [C-11]methane and iodine using a non-thermal plasma method. J. Labelled Compd. Radiopharm. 2006, 49, 1177-1186.
35. Welch, M. J.; Redvanly, C. Handbook of Radiopharmaceuticals Radiochemistry and Applications; Wiley: New York, 2003.
36. Jewett, D. M. A simple synthesis of [C-11] methyl triflate. Appl. Radiat. Isot. 1992, 43, 1383-1385.
37. Shiue, C. Y.; Bai, L. Q.; Teng, R. R.; Wolf, A. P. Syntheses of no-carrier-added (nca) [F-18] fluoroalkyl halides and their application in the syntheses of [F-18] fluoroalkyl derivatives of neurotransmitter receptor active compounds. J. Labelled Compd. Radiopharm. 1987, 24, 55-64.
38. Musachio, J. L.; Shah, J.; Pike, V. W. Radiosyntheses and reactivities of novel [F-18]2-fluoroethyl arylsulfonates. J. Labelled Compd. Radiopharm. 2005, 48, 735-747.
39. Andersson, Y.; Langstrom, B. Transition metal-mediated reactions using [C-11] cyanide in synthesis of C-11 labeled aromatic-compounds. J. Chem. Soc., Perkin Trans. 1 1994, 1395-1400.
40. Sandell, J.; Halldin, C.; Hall, H.; Thorberg, S. O.; Werner, T.; Sohn, D.; Sedvall, G.; Farde, L. Radiosynthesis and autoradiographic evaluation of [C-11]NAD-299, a radioligand for visualization of the 5-HT1A receptor. Nucl. Med. Biol. 1999, 26, 159-164.
41. Thorell, J. O.; Stoneelander, S.; Elander, N. Use of a microwave cavity to reduce reaction-times in radiolabeling with [C-11] cyanide. J. Labelled Compd. Radiopharm. 1992, 31, 207-217.
42. Boothe, T. E.; Finn, R. D.; Kothari, P. J.; Emran, A. M. Preparation of [C-11]carbon dioxide from [C-11] cyanide. Appl. Radiat. Isot. 1988, 39, 81-82.
43. Hara, T.; Iio, M. Online synthesis of [C-11] cyanide from cyclotron-produced [C-11] carbon-dioxide. Appl. Radiat. Isot. 1987, 38, 1092-1093.
44. Wilson, A. A.; Garcia, A.; Chestakova, A.; Kung, H.; Houle, S. A rapid one-step radiosynthesis of the beta-amyloid imaging radiotracer N-methyl-[C-11]2-(4′-methylaminophenyl)-6-hydroxybenzothiazole ([C-11]-O-OH-BTA-1). J. Labelled Compd. Radiopharm. 2004, 47, 679-682.
45. Petkova, A. T.; Ishii, Y.; Balbach, J. J.; Antzutkin, O. N.; Leapman, R. D.; Delaglio, F.; Tycko, R. A structural model for Alzheimer's beta-amyloid fibrils based on experimental constraints from solid state NMR. Proc. Natl. Acad. Sci. U.S.A 2002, 99, 16742-16747.
46. Chen, X. J. QSAR and primary docking studies of trans-stilbene (TSB) series of imaging agents for beta-amyloid plaques. J. Mol. Struct.: THEOCHEM 2006, 763, 83-89.
47. Le Pera, A.; Leggio, A.; Liguori, A. Highly specific N-monomethylation of primary aromatic amines. Tetrahedron 2006, 62, 6100-6106.
48. Esakkidurai, T.; Pitchumani, K. Zeolite-promoted selective mono-N-methylation of aniline with dimethyl carbonate. J. Mol. Catal. A: Chem. 2004, 218, 197-201.
49. Prashad, M.; Hu, B.; Har, D.; Repic, O.; Blacklock, T. J. A new, convenient and selective 4-dimethylaminopyridine-catalyzed trifluoroacetylation of anilines with ethyl trifluoroacetate. Tetrahedron Lett. 2000, 41, 9957-9961.
50. Collins, D. J.; Drygala, P. F.; Swan, J. M. Organophosphorus compounds. XVIII. Synthesis of 2-phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-sulfide by pyrolysis of (2-aminobenyl)phenyldithiophosphinic acid. Aust. J. Chem. 1983, 36, 2095-2110.
51. Beard, C. D.; Lee, V. J.; Whittle, C. E. Process for the Preparation of Aza-Annelated Pyrroles, Thiophenes and Furans as Potential Bioisosteres of Indole, Benzofuran and Benzothiophene Scaffolds. (CB Research and Development, Inc.) U.S. Patent 20060183758, 2006.