Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo(2. 2. 2)oct-3-yl alpha-hydroxy-alpha-(4-iodophenyl)-alpha- phenylacetate as potential radiopharmaceuticals

Journal Article · Wed Feb 01 04:00:00 EST 1984 · J. Med. Chem.; (United States)

DOI:https://doi.org/10.1021/jm00368a009· OSTI ID:7016312

Rzeszotarski, W J; Eckelman, W C; Francis, B E; Simms, D A; Gibson, R E; Jagoda, E M; Grissom, M P; Eng, R R; Conklin, J J; Reba, R C

Two derivatives of (RS)-1-azabicyclo(2.2.2)oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo(2.2.2)oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

• Research Organization: George Washington Univ. Medical Center, Washington, DC
• OSTI ID: 7016312
• Journal Information: J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 27:2; ISSN JMCMA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ACETONE
ARYL RADICALS
BETA DECAY RADIOISOTOPES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
DAYS LIVING RADIOISOTOPES
DRUGS
ELECTRON CAPTURE RADIOISOTOPES
HALOGENATION
HOURS LIVING RADIOISOTOPES
INTERMEDIATE MASS NUCLEI
IODINATION
IODINE 123
IODINE 125
IODINE ISOTOPES
ISOTOPES
KETONES
LABELLED COMPOUNDS
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
PHENYL RADICALS
RADICALS
RADIOISOTOPES
RADIOPHARMACEUTICALS
SYNTHESIS
TESTING
UPTAKE