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Novel selective catalytic reduction with tritium: synthesis of the GABA sub A receptor radioligand 1-(4-ethynylphenyl)-4-(2,3- sup 3 H sub 2 )propyl-2,6,7-trioxabicyclo(2. 2. 2 )octane

Abstract

Protection of the terminal alkyne function in 1-(4-ethynylphenyl)-4-(prop-2-enyl)-2,6,7-trioxabicyclo(2.2.2) octane with a trimethylsilyl group permits the selective catalytic reduction of the olefin moiety with tritium gas to give after deprotection 1-(4-ethynylphenyl)-4-(2,3-{sup 3}H{sub 2}) propyl-2,6,7-trioxabicyclo-(2.2.2) octane. The labeled product at high specific activity is an improved radioligand for the GABA-gated chloride channel of insects and mammals and the intermediate 4-(2,3-{sup 3}H{sub 2})propyl-1-(4-((trimethylsilyl)ethynyl)phenyl)-2,6,7-trioxabicyclo(2.2.2)octane is useful for studies on the metabolic activation of this selective proinsecticide. (author).
Authors:
Palmer, C J; Casida, J E [1] 
  1. California Univ., Berkeley, CA (United States). Pesticide Chemistry and Toxicology Lab.
Publication Date:
Jul 01, 1991
Product Type:
Journal Article
Reference Number:
AIX-23-014128; EDB-92-023075
Resource Relation:
Journal Name: Journal of Labelled Compounds and Radiopharmaceuticals; (United Kingdom); Journal Volume: 29:7
Subject:
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; CYCLOALKANES; LABELLING; TRITIUM COMPOUNDS; INSECTICIDES; AMINOBUTYRIC ACID; CHEMICAL PREPARATION; LIGANDS; RECEPTORS; ALKANES; AMINO ACIDS; AUTONOMIC NERVOUS SYSTEM AGENTS; CARBOXYLIC ACIDS; DRUGS; HYDROCARBONS; HYDROGEN COMPOUNDS; MEMBRANE PROTEINS; NEUROREGULATORS; ORGANIC ACIDS; ORGANIC COMPOUNDS; PESTICIDES; PROTEINS; SYNTHESIS; 400703* - Radiochemistry & Nuclear Chemistry- Radioisotope Production
OSTI ID:
6069732
Country of Origin:
United Kingdom
Language:
English
Other Identifying Numbers:
Journal ID: ISSN 0362-4803; CODEN: JLCRD; Other: CNN: N.I.H. P41 RR 01237-06
Submitting Site:
GBN
Size:
Pages: 829-839
Announcement Date:
Feb 15, 1992

Citation Formats

Palmer, C J, and Casida, J E. Novel selective catalytic reduction with tritium: synthesis of the GABA sub A receptor radioligand 1-(4-ethynylphenyl)-4-(2,3- sup 3 H sub 2 )propyl-2,6,7-trioxabicyclo(2. 2. 2 )octane. United Kingdom: N. p., 1991. Web. doi:10.1002/jlcr.2580290714.
Palmer, C J, & Casida, J E. Novel selective catalytic reduction with tritium: synthesis of the GABA sub A receptor radioligand 1-(4-ethynylphenyl)-4-(2,3- sup 3 H sub 2 )propyl-2,6,7-trioxabicyclo(2. 2. 2 )octane. United Kingdom. https://doi.org/10.1002/jlcr.2580290714
Palmer, C J, and Casida, J E. 1991. "Novel selective catalytic reduction with tritium: synthesis of the GABA sub A receptor radioligand 1-(4-ethynylphenyl)-4-(2,3- sup 3 H sub 2 )propyl-2,6,7-trioxabicyclo(2. 2. 2 )octane." United Kingdom. https://doi.org/10.1002/jlcr.2580290714.
@misc{etde_6069732,
title = {Novel selective catalytic reduction with tritium: synthesis of the GABA sub A receptor radioligand 1-(4-ethynylphenyl)-4-(2,3- sup 3 H sub 2 )propyl-2,6,7-trioxabicyclo(2. 2. 2 )octane}
author = {Palmer, C J, and Casida, J E}
abstractNote = {Protection of the terminal alkyne function in 1-(4-ethynylphenyl)-4-(prop-2-enyl)-2,6,7-trioxabicyclo(2.2.2) octane with a trimethylsilyl group permits the selective catalytic reduction of the olefin moiety with tritium gas to give after deprotection 1-(4-ethynylphenyl)-4-(2,3-{sup 3}H{sub 2}) propyl-2,6,7-trioxabicyclo-(2.2.2) octane. The labeled product at high specific activity is an improved radioligand for the GABA-gated chloride channel of insects and mammals and the intermediate 4-(2,3-{sup 3}H{sub 2})propyl-1-(4-((trimethylsilyl)ethynyl)phenyl)-2,6,7-trioxabicyclo(2.2.2)octane is useful for studies on the metabolic activation of this selective proinsecticide. (author).}
doi = {10.1002/jlcr.2580290714}
journal = []
volume = {29:7}
journal type = {AC}
place = {United Kingdom}
year = {1991}
month = {Jul}
}