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

• Published in: Bioorganic & medicinal chemistry letters Vol. 16; no. 8; pp. 2229 - 2233
• Main Authors: Gao, Mingzhang, Kong, Deyuan, Clearfield, Abraham, Zheng, Qi-Huang
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15.04.2006; Elsevier
• Subjects: 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptor; Amides - chemical synthesis; Amides - pharmacology; Animals; Anticonvulsants - chemical synthesis; Anticonvulsants - pharmacology; Anticonvulsants - therapeutic use; Biological and medical sciences; Brain diseases; Carbon - chemistry; Carbon-11; Contrast media. Radiopharmaceuticals; Fluorine - chemistry; Fluorine-18; Isoquinolines - chemical synthesis; Isoquinolines - pharmacology; Isoquinolines - therapeutic use; Isotope Labeling; Ligands; Medical sciences; Mice; Molecular Structure; N-Acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives; Pharmacology. Drug treatments; Positron emission tomography; Receptors, AMPA - antagonists & inhibitors; Seizures - drug therapy; Carbon-11; Fluorine-18; Positron emission tomography; 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptor; N-Acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives; Brain diseases; Fluorine Isotopes; Isoquinoline derivatives; Fluorine 18; Radiolabelling; Ligand; Central nervous system; Carbon Isotopes; Glutamate receptor; AMPA receptor; Carbon 11; N-Acetyl-l-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives; Chemical synthesis; Crystalline structure
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2006.01.042

New carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives were designed and synthesized as potential positron emission tomography AMPA (2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid) receptor ligands to image brain diseases. The single crystal structure of the most potent compound N-acetyl-1-(4′-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ( 5a) is first reported.