Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid
Publication type: Journal Article
Publication date: 1990-08-01
scimago Q3
wos Q4
SJR: 0.271
CiteScore: 2.0
Impact factor: 0.9
ISSN: 03624803, 10991344
Organic Chemistry
Drug Discovery
Biochemistry
Spectroscopy
Analytical Chemistry
Radiology, Nuclear Medicine and imaging
Abstract
A method is described for the synthesis, purification and radiolabelling of 2-{5-(4-iodophenyl)pentyl}oxirane-2-carboxylic acid (I-POCA). This new compound was synthesized from 5-phenyl-pentylbromide (1), prepared via 5-phenyl-1-pentanol and subsequently converted to diethyl 5-phenylpentylmalonate (2). The latter on alkaline hydrolysis yielded ethyl 5-phenyl-pentylmalonate (3). Para-substitution of iodine on the phenyl moiety of the monoester (3) was accomplished by reacting compound (3) with thallium trifluoroacetate (TTFA) and subsequently with KI. Oxidation of ethyl 7-(4-iodophenyl)-2-methyleneheptanoate (5), which was synthesized from the monoester, ethyl 5-(4-iodophenyl)pentylmalonate (4) yielded ethyl 2-{5-(4-iodophenyl)pentyl}oxirane-2-carboxylate (6). The radiolabelling procedure was based on a Cu(I)Cl-assisted, isotopic exchange reaction, which produced a no-carrier-added and regiospecific radioiodination with a 32-52% radiochemical yield.
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Abbas H G, Hankes L. V., Feinendegen L. E. Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid // Journal of Labelled Compounds and Radiopharmaceuticals. 1990. Vol. 28. No. 8. pp. 955-966.
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Abbas H G, Hankes L. V., Feinendegen L. E. Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid // Journal of Labelled Compounds and Radiopharmaceuticals. 1990. Vol. 28. No. 8. pp. 955-966.
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TY - JOUR
DO - 10.1002/jlcr.2580280809
UR - https://doi.org/10.1002/jlcr.2580280809
TI - Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid
T2 - Journal of Labelled Compounds and Radiopharmaceuticals
AU - Abbas H G
AU - Hankes, L. V.
AU - Feinendegen, L. E.
PY - 1990
DA - 1990/08/01
PB - Wiley
SP - 955-966
IS - 8
VL - 28
SN - 0362-4803
SN - 1099-1344
ER -
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@article{1990_Abbas H G,
author = {Abbas H G and L. V. Hankes and L. E. Feinendegen},
title = {Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid},
journal = {Journal of Labelled Compounds and Radiopharmaceuticals},
year = {1990},
volume = {28},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/jlcr.2580280809},
number = {8},
pages = {955--966},
doi = {10.1002/jlcr.2580280809}
}
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MLA
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Abbas H. G., et al. “Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid.” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 28, no. 8, Aug. 1990, pp. 955-966. https://doi.org/10.1002/jlcr.2580280809.