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Synthesis of an (iodovinyl)misonidazole derivative for hypoxia imaging.

Abstract：

:Nitroimidazoles undergo a bioreduction in viable hypoxic tissue, resulting in trapping within these tissues, as demonstrated by misonidazole. A radioiodinated analogue of misonidazole (IVM, (E)-5-(2-Nitroimidazolyl)-4-hydroxy-1-iodopent-1-ene, 3) has been synthesized by halodestannylation, for evaluation as an imaging agent for hypoxia. A key step in the synthetic sequence involves the use of the Lewis acid BF3.Et2O to promote the nucleophilic ring opening of glycidyl tosylate with (E)-1-lithio-2-(tributylstannyl)ethylene. Direct comparison of IVM versus F-MISO (2) another misonidazole type hypoxic cell marker, in several in vitro cell culture studies, indicates that IVM behaves in analogous fashion to F-MISO and has promise as a hypoxia imaging agent for SPECT.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Biskupiak JE,Grierson JR,Rasey JS,Martin GV,Krohn KA

doi

10.1021/jm00111a036

subject

Has Abstract

pub_date

1991-07-01 00:00:00

pages

2165-8

issue

7

eissn

0022-2623

issn

1520-4804

journal_volume

34

pub_type

杂志文章

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