Synthesis of carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7- dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as new potential PET AMPA receptor ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 8, 2006, Pages 2229-2233

  Gao, Mingzhang ^a   Kong, Deyuan ^b   Clearfield, Abraham ^b   Zheng, Qi Huang ^a  

^a INDIANA UNIVERSITY   (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

2 Amino 3 (3 hydroxy 5 methylisoxazol 4 yl)propionic acid receptor; Brain diseases; Carbon 11; Fluorine 18; N Acetyl 1 aryl 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline derivatives; Positron emission tomography

Indexed keywords

AMPA RECEPTOR; CARBON 11; FLUORINE 18; N ACETYL 1 (3' CHLOROPHENYL) 6 HYDROXY 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (3' CHLOROPHENYL) 6 HYDROXY 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 1 (3' CHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (3' CHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 1 (3',4' DICHLOROPHENYL) 6 HYDROXY 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (3',4' DICHLOROPHENYL) 6 HYDROXY 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 1 (3',4' DICHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (3',4' DICHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 1 (4' CHLOROPHENYL) 6 HYDROXY 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (4' CHLOROPHENYL) 6 HYDROXY 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 1 (4' CHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (4' CHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 1 (4' CHLOROPHENYL) 7 HYDROXY 6 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 1 (4' CHLOROPHENYL) 7 HYDROXY 6 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 6,7 DIMETHOXY 1 (4' FLUOROPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 6,7 DIMETHOXY 1 (4' FLUOROPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 6,7 DIMETHOXY 1 (4' HYDROXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 6,7 DIMETHOXY 1 (4' HYDROXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 6,7 DIMETHOXY 1 (4' METHOXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 6,7 DIMETHOXY 1 (4' METHOXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; N ACETYL 6,7 DIMETHOXY 1 (4' NITROPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE C 11; N ACETYL 6,7 DIMETHOXY 1 (4' NITROPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE F 18; RADIOPHARMACEUTICAL AGENT; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BRAIN DISEASE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; LIGAND BINDING; NEUROIMAGING; POSITRON EMISSION TOMOGRAPHY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMIDES; ANIMALS; ANTICONVULSANTS; CARBON; FLUORINE; ISOQUINOLINES; ISOTOPE LABELING; LIGANDS; MICE; MOLECULAR STRUCTURE; POSITRON-EMISSION TOMOGRAPHY; RECEPTORS, AMPA; SEIZURES;

EID: 33644813372     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.01.042     Document Type: Article

References (14)

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8. 2 Sep-Pak type cartridge was obtained from Waters Corporate Headquarters, Milford, MA. Sterile vented Millex-GS 0.22 μm filter unit was obtained from Millipore Corporation, Bedford, MA.
9. 3), 5.03 (s, 1H, H-1), 6.20 (s, 1H, H-5), 6.63 (s, 1H, H-8), 6.96-7.03 (m, 2H, ArH), 7.20-7.25 (m, 2H, ArH).
10. 3), 6.48 (s, 1H, H-1), 6.66 (s, 1H, H-5), 6.85 (s, 1H, H-8), 6.95 (t, J = 8.45 Hz, 2H, ArH), 7.21 (dd, J = 5.51, 8.09 Hz, 2H, ArH).
11. 3 331.0970, found 331.0962.
12. 11C]5e were >93%.
13. 18F]5g was ∼92%.
14. X-ray crystallography. The crystallographic measurements were carried out on a Siemens P4 diffractometer with graphite-monochromated Mo-Kα radiation (λ = 0.71073 Å) and 12-kW rotating generator. The data were collected at 110 K. The structure was solved and refined using the programs SHELXS-97 (Sheldrick, 1997) and SHELXL (Sheldrick 1997). The program X-Seed (Barbour, 1999) was used as an interface to the SHELX programs. X-ray coordinates have been deposited with the Cambridge Crystallographic Data Centre (CCDC) for small molecules and the deposition number is CCDC 294643.